Synergistic weed control from applications of pyridine carboxylic acid herbicides and synthetic auxin herbicides and/or auxin transport inhibitors

ABSTRACT

Disclosed herein are herbicidal compositions comprising a herbicidally effective amount of (a) a pyridine carboxylic acid herbicide or an agriculturally acceptable N-oxide, salt or ester thereof, and (b) a synthetic auxin herbicide, an auxin transport inhibitor, agriculturally acceptable salts or esters thereof, or combinations thereof. Also disclosed herein are methods of controlling undesirable vegetation which comprise applying to vegetation or an area adjacent the vegetation or applying to soil or water to prevent the emergence or growth of vegetation (a) a pyridine carboxylic acid herbicide or an agriculturally acceptable N-oxide, salt or ester thereof, and (b) a synthetic auxin herbicide, an auxin transport inhibitor, agriculturally acceptable salts or esters thereof, or combinations thereof, wherein (a) and (b) are each added in an amount sufficient to provide a herbicidal effect.

CROSS REFERENCE TO RELATED APPLICATIONS

This application claims benefit of U.S. Provisional Patent Application No. 62/050,719, filed Sep. 15, 2014, and U.S. Provisional Patent Application No. 62/050,710, filed Sep. 15, 2014, which are hereby incorporated herein by reference in their entireties.

FIELD OF THE DISCLOSURE

The present disclosure relates to herbicidal compositions comprising a herbicidally effective amount of (a) a pyridine carboxylic acid herbicide or an agriculturally acceptable N-oxide salt or ester thereof, and (b) a synthetic auxin herbicide, an auxin transport inhibitor, agriculturally acceptable salts or esters thereof, or combinations thereof. The present disclosure also relates to methods for controlling undesirable vegetation.

BACKGROUND

Many recurring problems in agriculture involve controlling growth of undesirable vegetation that can, for instance, inhibit crop growth. To help control undesirable vegetation, researchers have produced a variety of chemicals and chemical formulations effective in controlling such unwanted growth. However, a continuing need exists for new compositions and methods to control growth of undesirable vegetation.

SUMMARY OF THE DISCLOSURE

Disclosed herein are herbicidal compositions comprising a herbicidally effective amount of (a) a pyridine carboxylic acid herbicide or an agriculturally acceptable N-oxide, salt, or ester thereof, and (b) a synthetic auxin herbicide, auxin transport inhibitor, agriculturally acceptable salts or esters thereof, or combinations thereof. In some embodiments, (a) and (b) can be provided in a synergistic herbicidally effective amount. In some embodiments, (b) can comprise a synthetic auxin herbicide or an agriculturally acceptable salt or ester thereof, and the weight ratio of (a) to (b) can be from 1:8000 to 30:1 (e.g., 1:3000 to 60:1, from 1:2225 to 30:1, from 1:200 to 8:1, from 1:70 to 1:1, or from 1:85 to 3.5:1). In some embodiments, (b) can comprise an auxin transport inhibitor, or an agriculturally acceptable salt or ester thereof, and the weight ratio of (a) to (b) can be from 1:1000 to 85:1 (e.g., 1:200 to 12:1, from 1:30 to 5:1, from 1:2 to 12:1, from 1:1 to 6:1, or from 1.25:1 to 5:1).

The pyridine carboxylic acid herbicide can comprise a compound defined by Formula (I)

wherein

X is N or CY, wherein Y is hydrogen, halogen, C₁-C₃ alkyl, C₁-C₃ haloalkyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio or C₁-C₃ haloalkylthio; R¹ is OR^(1′) or NR^(1″)R^(1″′), wherein R^(1′) is hydrogen, C₁-C₈ alkyl, C₁-C₆ haloalkyl, or C₇-C₁₀ arylalkyl, and R^(1″) and R^(1″′) are independently hydrogen, C₁-C₁₂ alkyl, C₃-C₁₂ alkenyl, or C₃-C₁₂ alkynyl;

R² is hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄ haloalkylamino, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, cyano, or a group of the formula —CR¹⁷═CR¹⁸—SiR¹⁹R²⁰R²¹, wherein R¹⁷ is hydrogen, F, or Cl; R¹⁸ is hydrogen, F, Cl, C₁-C₄ alkyl, or C₁-C₄ haloalkyl; and R¹⁹, R²⁰, and R²¹ are independently C₁-C₁₀ alkyl, C₃-C₆ cycloalkyl, phenyl, substituted phenyl, C₁-C₁₀ alkoxy, or OH; R³ and R⁴ are independently hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆ alkylsulfonyl, C₁-C₆ trialkylsilyl, C₁-C₆ dialkylphosphonyl, or R³ and R⁴ taken together with N is a 5- or 6-membered saturated ring, or R³ and R⁴ taken together represent ═CR^(3′)(R^(4′)), wherein R^(3′) and R^(4′) are independently hydrogen, C₁-C₆ alkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl, C₁-C₆ alkoxy or C₁-C₆ alkylamino, or, R^(3′) and R^(4′) taken together with ═C represent a 5- or 6-membered saturated ring;

A is one of groups A1 to A36

R⁵, if applicable to the A group, is hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄ haloalkylamino, OH, or CN;

R⁶, R^(6′), and R⁶″, if applicable to the A group, are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino or C₂-C₄ haloalkylamino, OH, CN, or NO₂;

R⁷ and R^(7′) are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, C₁-C₄ haloalkylamino, or phenyl;

R⁸ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆ alkylsulfonyl, C₁-C₆ trialkylsilyl, or phenyl;

or an agriculturally acceptable N-oxide or salt thereof.

In some embodiments, A is A1, A2, A3, A7, A8, A9, A10, A11, A12, A13, A14, or A15. In some cases, A is A1, A2, A3, A7, A8, A9, A10, A13, A14, or A15. In certain cases, A is A2, A3, A8, A13, or A15.

In certain embodiments, the pyridine carboxylic acid herbicide can comprise a compound defined by Formula (II):

wherein

R¹ is OR^(1′) or NR^(1″)R^(1″′), wherein R^(1′) is hydrogen, C₁-C₈ alkyl, C₁-C₆ haloalkyl, or C₇-C₁₀ arylalkyl, and R^(1″) and R^(1″′) are independently hydrogen, C₁-C₁₂ alkyl, C₃-C₁₂ alkenyl, or C₃-C₁₂ alkynyl;

R² is hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄ haloalkylamino, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, cyano, or a group of the formula —CR¹⁷═CR¹⁸—SiR¹⁹R²⁰R²¹, wherein R¹⁷ is hydrogen, F, or Cl; R¹⁸ is hydrogen, F, Cl, C₁-C₄ alkyl, or C₁-C₄ haloalkyl; and R¹⁹, R²⁰, and R²¹ are independently C₁-C₁₀ alkyl, C₃-C₆ cycloalkyl, phenyl, substituted phenyl, C₁-C₁₀ alkoxy, or OH;

R³ and R⁴ are independently hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆ alkylsulfonyl, C₁-C₆ trialkylsilyl, C₁-C₆ dialkylphosphonyl, or R³ and R⁴ taken together with N is a 5- or 6-membered saturated ring, or R³ and R⁴ taken together represent ═CR^(3′)(R^(4′)), wherein R^(3′) and R^(4′) are independently hydrogen, C₁-C₆ alkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl, C₁-C₆ alkoxy or C₁-C₆ alkylamino, or, R^(3′) and R^(4′) taken together with ═C represent a 5- or 6-membered saturated ring;

A is A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15, A16, A17, A18, A19, A20, A21, A22, A23, A24, A25, A26, A27, A28, A29, A30, A31, A32, A33, A34, A35, or A36;

R⁵ is hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄ haloalkylamino, OH, or CN;

R⁶, R^(6′), and R^(6″) are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino or C₂-C₄ haloalkylamino, OH, CN, or NO₂;

R⁷ and R^(7′) are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄ haloalkylamino, or phenyl; and

R⁸ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆ alkylsulfonyl, C₁-C₆ trialkylsilyl, or phenyl;

or an agriculturally acceptable N-oxide or salt thereof.

In some embodiments, R¹ is OR^(1′), wherein R^(1′) is hydrogen, C₁-C₈ alkyl, or C₇-C₁₀ arylalkyl. In certain embodiments, R² is Cl, methoxy, vinyl, or 1-propenyl; R³ and R⁴ are hydrogen; A is A15; R⁵ is hydrogen or F; R⁶ is hydrogen or F; and R⁶″ is hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl, C₂-C₄ alkynyl, CN, or NO₂.

In certain embodiments, the pyridine carboxylic acid herbicide can comprise a compound defined by Formula (III):

wherein

X is N or CY, wherein Y is hydrogen, halogen, C₁-C₃ alkyl, C₁-C₃ haloalkyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio or C₁-C₃ haloalkylthio;

R¹ is OR^(1′) or NR^(1″)R^(1″′), wherein R^(1′) is hydrogen, C₁-C₈ alkyl, C₁-C₆ haloalkyl, or C₇-C₁₀ arylalkyl, and R^(1″) and R^(1″′) are independently hydrogen, C₁-C₁₂ alkyl, C₃-C₁₂ alkenyl, or C₃-C₁₂ alkynyl;

R² is hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄ haloalkylamino, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, cyano, or a group of the formula —CR¹⁷═CR¹⁸—SiR¹⁹R²⁰R²¹, wherein R¹⁷ is hydrogen, F, or Cl; R¹⁸ is hydrogen, F, Cl, C₁-C₄ alkyl, or C₁-C₄ haloalkyl; and R¹⁹, R²⁰, and R²¹ are independently C₁-C₁₀ alkyl, C₃-C₆ cycloalkyl, phenyl, substituted phenyl, C₁-C₁₀ alkoxy, or OH;

R³ and R⁴ are independently hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆ alkylsulfonyl, C₁-C₆ trialkylsilyl, C₁-C₆ dialkylphosphonyl, or R³ and R⁴ taken together with N is a 5- or 6-membered saturated ring, or R³ and R⁴ taken together represent ═CR^(3′)(R^(4′)), wherein R^(3′) and R^(4′) are independently hydrogen, C₁-C₆ alkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl, C₁-C₆ alkoxy or C₁-C₆ alkylamino, or, R^(3′) and R^(4′) taken together with ═C represent a 5- or 6-membered saturated ring;

R⁶ and R^(6′) are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino or C₂-C₄ haloalkylamino, OH, CN, or NO₂;

R⁷ and R^(7′) are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄ haloalkylamino, or phenyl; and

R⁸ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆ alkylsulfonyl, C₁-C₆ trialkylsilyl, or phenyl;

or an agriculturally acceptable N-oxide or salt thereof.

In some embodiments, X is N, CH or CF. In certain embodiments, X is CF, R¹ is OR^(1′), wherein R^(1′) is hydrogen, C₁-C₈ alkyl, or C₇-C₁₀ arylalkyl; R² is Cl, methoxy, vinyl, or 1-propenyl; R³ and R⁴ are hydrogen; R⁶ is hydrogen or F; and R^(6′) is hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl, C₂-C₄ alkynyl, CN, or NO₂.

In certain embodiments, the pyridine carboxylic acid herbicide can comprise a compound defined by Formula (IV):

wherein

X is N or CY, wherein Y is hydrogen, halogen, C₁-C₃ alkyl, C₁-C₃ haloalkyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio or C₁-C₃ haloalkylthio;

R¹ is OR^(1′) or NR^(1″)R^(1″′), wherein R^(1′) is hydrogen, C₁-C₈ alkyl, C₁-C₆ haloalkyl, or C₇-C₁₀ arylalkyl, and R^(1″) and R^(1″′) are independently hydrogen, C₁-C₁₂ alkyl, C₃-C₁₂ alkenyl, or C₃-C₁₂ alkynyl;

R² is hydrogen, F, Br, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄ haloalkylamino, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, cyano, or a group of the formula —CR¹⁷═CR¹⁸—SiR¹⁹R²⁰R²¹, wherein R¹⁷ is hydrogen, F, or Cl; R¹⁸ is hydrogen, F, Cl, C₁-C₄ alkyl, or C₁-C₄ haloalkyl; and R¹⁹, R²⁰, and R²¹ are independently C₁-C₁₀ alkyl, C₃-C₆ cycloalkyl, phenyl, substituted phenyl, C₁-C₁₀ alkoxy, or OH;

R³ and R⁴ are independently hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆ alkylsulfonyl, C₁-C₆ trialkylsilyl, C₁-C₆ dialkylphosphonyl, or R³ and R⁴ taken together with N is a 5- or 6-membered saturated ring, or R³ and R⁴ taken together represent ═CR^(3′)(R^(4′)), wherein R^(3′) and R^(4′) are independently hydrogen, C₁-C₆ alkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl, C₁-C₆ alkoxy or C₁-C₆ alkylamino, or, R^(3′) and R^(4′) taken together with ═C represent a 5- or 6-membered saturated ring;

A is A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15, A16, A17, A18, A19, A20, A21, A22, A23, A24, A25, A26, A27, A28, A29, A30, A31, A32, A33, A34, A35, or A36;

R⁵ is hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄ haloalkylamino, OH, or CN;

R⁶, R^(6′), and R⁶″ are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino or C₂-C₄ haloalkylamino, OH, CN, or NO₂;

R⁷ and R^(7′) are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄ haloalkylamino, or phenyl; and

R⁸ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆ alkylsulfonyl, C₁-C₆ trialkylsilyl, or phenyl;

or an agriculturally acceptable N-oxide or salt thereof.

In some embodiments, R² is C₂-C₄-alkenyl, C₂-C₄ haloalkenyl, or C₁-C₄-alkoxy. In certain embodiments, R² is methoxy, vinyl, 1-fluorovinyl, or 1-propenyl. In some cases, R³ and R⁴ are hydrogen. In some embodiments, A is A1, A2, A3, A7, A8, A9, A10, A13, A14, or A15.

In certain cases, A is A2, A3, A8, A13, or A15. In certain cases, A is A1, A2, A3, A13, A14, or A15.

In certain embodiments, the pyridine carboxylic acid herbicide can include 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl) picolinic acid, or an agriculturally acceptable N-oxide, salt, or ester thereof.

In some embodiments, (b) can comprise a phenoxy herbicide, a benzoic acid herbicide, a carboxylic acid herbicide, agriculturally acceptable salts and esters thereof, or a combination thereof. In certain embodiments, (b) can include 2,4-D, 2,4-DB, MCPA, MCPB, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoro-2-pyridinecarboxylic acid, benzyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoro-2-pyridinecarboxylate, aminocyclopyrachlor, aminopyralid, chloramben, clomeprop, dichlorprop, mecoprop, dicamba, clopyralid, fluroxypyr, halauxifen, halauxifen-methyl, picloram, quinclorac, quinmerac, triclopyr, agriculturally acceptable salts and esters thereof, or a combination thereof.

In some embodiments, (b) can comprise a semicarbazone herbicide, phthalamate herbicide, or other benzoic acid, agriculturally acceptable salts and esters thereof, or a combination thereof. In certain embodiments, (b) can include diflufenzopyr, naptalam, 2,3,5-triiodobenzoic acid, agriculturally acceptable salts and esters thereof, or a combination thereof.

The composition can further comprise an additional pesticide, a herbicidal safener, an agriculturally acceptable adjuvant or carrier, or a combination thereof. The composition can be provided as a herbicidal concentrate. In certain embodiments, the active ingredients in the composition consist of (a) and (b).

The present disclosure also relates to methods of controlling undesirable vegetation which comprise applying to vegetation or an area adjacent the vegetation or applying to soil or water to prevent the emergence or growth of vegetation a herbicidally effective amount of (a) a pyridine carboxylic acid herbicide or an agriculturally acceptable N-oxide, salt, or ester thereof, and (b) a synthetic auxin herbicide, an auxin transport inhibitor, agriculturally acceptable salts or esters thereof, or combinations thereof. In some embodiments, (a) and (b) are provided in a synergistically effective amount. In some embodiments, (a) and (b) are applied simultaneously. In some embodiments, (a) and (b) are applied post-emergence of the undesirable vegetation.

In some embodiments, (a) can comprise a pyridine carboxylic acid herbicide described above. In certain embodiments, (a) can comprise 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl) picolinic acid or an agriculturally acceptable N-oxide, salt, or ester thereof. In some cases, (a) can be applied in an amount of from 0.1 grams acid equivalent per hectare (g ae/ha) to 300 g ae/ha (e.g., from 0.5 g ae/ha to 300 g ae/ha, from 5 g ae/ha to 40 g ae/ha).

In some embodiments, (b) can comprise a phenoxy herbicide, benzoic acid herbicide, carboxylic acid herbicide, agriculturally acceptable salts and esters thereof, or a combination thereof. In certain embodiments, (b) can include 2,4-D, 2,4-DB, MCPA, MCPB, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoro-2-pyridinecarboxylic acid, benzyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoro-2-pyridinecarboxylate, aminocyclopyrachlor, aminopyralid, chloramben, clomeprop, dichlorprop, mecoprop, dicamba, clopyralid, fluroxypyr, halauxifen, halauxifen-methyl, picloram, quinclorac, quinmerac, triclopyr, agriculturally acceptable salts and esters thereof, or a combination thereof. In some cases, (a) can be applied in an amount of from 0.1 g ae/ha to 300 g ae/ha (e.g., from 0.5 g ae/ha, from 5 g ae/ha to 40 g ae/ha) and/or (b) can be applied in an amount of from 5 g ae/ha to 3000 g ae/ha (e.g., from 5 g ae/ha to 1000 g ae/ha). In some cases, (a) and (b) can be applied in a weight ratio of from 1:8800 to 240:1 (e.g., from 1:3000 to 60:1, from 1:224 to 4:1, from 1:200 to 8:1, from 1:70 to 1:1, or from 1:56 to 1:1).

In some embodiments, (b) can comprise a semicarbazone herbicide. In certain embodiments, (b) can include diflufenzopyr or an agriculturally acceptable salt or ester thereof. In some cases, (a) can be applied in an amount of from 0.1 g ae/ha to 300 g ae/ha (e.g., from 0.5 g ae/ha, from 5 g ae/ha to 40 g ae/ha) and/or (b) can be applied in an amount of from 1 g ae/ha to 1000 g ae/ha (e.g., from 3.5 g ae/ha to 15 g ae/ha). In some cases, (a) and (b) can be applied in a weight ratio of from 1:2000 to 300:1 (e.g., 1:200 to 12:1, from 1:100 to 10:1, from 1:25 to 5:1, from 1:2 to 12:1, from 1:1 to 6:1, from 1:3.3 to 1:2, or from 1.25:1 to 5:1).

In some embodiments, (b) can comprise a phthalamate herbicide or other benzoic acid, agriculturally acceptable salts or esters thereof. In certain embodiments, (b) can include naptalam, 2,3,5-triiodobenzoic acid, or an agriculturally acceptable salt or ester thereof. In some cases, (a) can be applied in an amount of from 0.1 g ae/ha to 300 g ae/ha (e.g., from 0.5 g ae/ha, from 5 g ae/ha to 40 g ae/ha) and/or (b) can be applied in an amount of from 2000 g ae/ha to 5000 g ae/ha (e.g., from 2000 g ae/ha to 3500 g ae/ha). In some cases, (a) and (b) can be applied in a weight ratio of from 1:11000 to 1:6.7 (e.g., from 1:4000 to 1:18.3, from 1:2000 to 1:25, or from 1:1000 to 1:50).

The description below sets forth details of one or more embodiments of the present disclosure. Other features, objects, and advantages will be apparent from the description and from the claims.

DETAILED DESCRIPTION

The present disclosure relates to herbicidal compositions comprising a herbicidally effective amount of (a) a pyridine carboxylic acid herbicide or an agriculturally acceptable N-oxide, salt, or ester thereof, and (b) a synthetic auxin herbicide, an auxin transport inhibitor, agriculturally acceptable salts or esters thereof, or a combination thereof. The present disclosure also relates to methods for controlling undesirable vegetation.

I. Definitions

Terms used herein will have their customary meaning in the art unless specified otherwise. The organic moieties mentioned when defining variable positions within the general formulae described herein (e.g., the term “halogen”) are collective terms for the individual substituents encompassed by the organic moiety. The prefix C_(n)-C_(m) preceding a group or moiety indicates, in each case, the possible number of carbon atoms in the group or moiety that follows.

As used herein, the terms “herbicide” and “herbicidal active ingredient” refer to an active ingredient that kills, controls, or otherwise adversely modifies the growth of vegetation, particularly undesirable vegetation, such as weeds, when applied in an appropriate amount.

As used herein, a herbicidally effective amount” refers to an amount of an active ingredient that causes a “herbicidal effect,” i.e., an adversely modifying effect including, for instance, a deviation from natural growth or development, killing, regulation, desiccation, growth inhibition, growth reduction, and retardation.

As used herein, applying a herbicide or herbicidal composition refers to delivering it directly to the targeted vegetation or to the locus thereof or to the area where control of undesired vegetation is desired. Methods of application include, but are not limited to pre-emergently contacting soil or water, post-emergently contacting the undesirable vegetation or area adjacent to the undesirable vegetation.

As used herein, the terms “crops” and “vegetation” can include, for instance, dormant seeds, germinant seeds, emerging seedlings, plants emerging from vegetative propagules, immature vegetation, and established vegetation.

As used herein, immature vegetation refers to small vegetative plants prior to reproductive stage, and mature vegetation refers to vegetative plants during and after the reproductive stage.

As used herein, the term “acyl” refers to a group of formula —C(O)R, where R is hydrogen, alkyl (e.g., C₁-C₁₀ alkyl), haloalkyl (C₁-C₈ haloalkyl), alkenyl (C₂-C₈ alkenyl), haloalkenyl (e.g., C₂-C₈ haloalkenyl), alkynyl (e.g., C₂-C₈ alkynyl), alkoxy (C₁-C₈ alkoxy), haloalkoxy (C₁-C₈ alkoxy), aryl, or heteroaryl, arylalkyl (C₇-C₁₀ arylalkyl), as defined below, where “C(O)” or “CO” is short-hand notation for C═O. In some embodiments, the acyl group can be a C₁-C₆ acyl group (e.g., a formyl group, a C₁-C₅ alkylcarbonyl group, or a C₁-C₅ haloalkylcarbonyl group). In some embodiments, the acyl group can be a C₁-C₃ acyl group (e.g., a formyl group, a C₁-C₃ alkylcarbonyl group, or a C₁-C₃ haloalkylcarbonyl group).

As used herein, the term “alkyl” refers to saturated, straight-chained or branched saturated hydrocarbon moieties. Unless otherwise specified, C₁-C₂₀ (e.g., C₁-C₁₂, C₁-C₁₀, C₁-C₈, C₁-C₆, C₁-C₄) alkyl groups are intended. Examples of alkyl groups include methyl, ethyl, propyl, 1-methyl-ethyl, butyl, 1-methyl-propyl, 2-methyl-propyl, 1,1-dimethyl-ethyl, pentyl, 1-methyl-butyl, 2-methyl-butyl, 3-methyl-butyl, 2,2-dimethyl-propyl, 1-ethyl-propyl, hexyl, 1,1-dimethyl-propyl, 1,2-dimethyl-propyl, 1-methyl-pentyl, 2-methyl-pentyl, 3-methyl-pentyl, 4-methyl-pentyl, 1,1-dimethyl-butyl, 1,2-dimethyl-butyl, 1,3-dimethyl-butyl, 2,2-dimethyl-butyl, 2,3-dimethyl-butyl, 3,3-dimethyl-butyl, 1-ethyl-butyl, 2-ethyl-butyl, 1,1,2-trimethyl-propyl, 1,2,2-trimethyl-propyl, 1-ethyl-1-methyl-propyl, and 1-ethyl-2-methyl-propyl. Alkyl substituents may be unsubstituted or substituted with one or more chemical moieties. Examples of suitable substituents include, for example, hydroxy, nitro, cyano, formyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₁-C₆ acyl, C₁-C₆ alkylthio, C₁-C₆ haloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆ haloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ haloalkoxycarbonyl, C₁-C₆ carbamoyl, C₁-C₆ halocarbamoyl, hydroxycarbonyl, C₁-C₆ alkylcarbonyl, C₁-C₆ haloalkylcarbonyl, aminocarbonyl, C₁-C₆ alkylaminocarbonyl, haloalkylaminocarbonyl, C₁-C₆ dialkylaminocarbonyl, and C₁-C₆ dihaloalkylaminocarbonyl, provided that the substituents are sterically compatible and the rules of chemical bonding and strain energy are satisfied. Preferred substituents include cyano and C₁-C₆ alkoxy.

As used herein, the term “haloalkyl” refers to straight-chained or branched alkyl groups, wherein these groups the hydrogen atoms may partially or entirely be substituted with halogen atoms. Unless otherwise specified, C₁-C₂₀ (e.g., C₁-C₁₂, C₁-C₁₀, C₁-C₈, C₁-C₆, C₁-C₄) haloalkyl groups are intended. Examples include chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, and 1,1,1-trifluoroprop-2-yl. Haloalkyl substituents may be unsubstituted or substituted with one or more chemical moieties. Examples of suitable substituents include, for example, hydroxy, nitro, cyano, formyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₁-C₆ acyl, C₁-C₆ alkylthio, C₁-C₆ haloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆ haloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ haloalkoxycarbonyl, C₁-C₆ carbamoyl, C₁-C₆ halocarbamoyl, hydroxycarbonyl, C₁-C₆ alkylcarbonyl, C₁-C₆ haloalkylcarbonyl, aminocarbonyl, C₁-C₆ alkylaminocarbonyl, haloalkylaminocarbonyl, C₁-C₆ dialkylaminocarbonyl, and C₁-C₆ dihaloalkylaminocarbonyl, provided that the substituents are sterically compatible and the rules of chemical bonding and strain energy are satisfied. Preferred substituents include cyano and C₁-C₆ alkoxy.

As used herein, the term “alkenyl” refers to unsaturated, straight-chained, or branched hydrocarbon moieties containing a double bond. Unless otherwise specified, C₂-C₂₀ (e.g., C₂-C₁₂, C₂-C₁₀, C₂-C₈, C₂-C₆, C₂-C₄) alkenyl groups are intended. Alkenyl groups may contain more than one unsaturated bond. Examples include ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl, and 1-ethyl-2-methyl-2-propenyl. The term “vinyl” refers to a group having the structure —CH═CH₂; 1-propenyl refers to a group with the structure-CH═CH—CH₃; and 2-propenyl refers to a group with the structure —CH₂—CH═CH₂. Alkenyl substituents may be unsubstituted or substituted with one or more chemical moieties. Examples of suitable substituents include, for example, hydroxy, nitro, cyano, formyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₁-C₆ acyl, C₁-C₆ alkylthio, C₁-C₆ haloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆ haloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ haloalkoxycarbonyl, C₁-C₆ carbamoyl, C₁-C₆ halocarbamoyl, hydroxycarbonyl, C₁-C₆ alkylcarbonyl, C₁-C₆ haloalkylcarbonyl, aminocarbonyl, C₁-C₆ alkylaminocarbonyl, haloalkylaminocarbonyl, C₁-C₆ dialkylaminocarbonyl, and C₁-C₆ dihaloalkylaminocarbonyl, provided that the substituents are sterically compatible and the rules of chemical bonding and strain energy are satisfied. Preferred substituents include cyano and C₁-C₆ alkoxy.

The term “haloalkenyl,” as used herein, refers to an alkenyl group, as defined above, which is substituted by one or more halogen atoms.

As used herein, the term “alkynyl” represents straight-chained or branched hydrocarbon moieties containing a triple bond. Unless otherwise specified, C₂-C₂₀ (e.g., C₂-C₁₂, C₂-C₁₀, C₂-C₈, C₂-C₆, C₂-C₄) alkynyl groups are intended. Alkynyl groups may contain more than one unsaturated bond. Examples include C₂-C₆-alkynyl, such as ethynyl, 1-propynyl, 2-propynyl (or propargyl), 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 3-methyl-1-butynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 3-methyl-1-pentynyl, 4-methyl-1-pentynyl, 1-methyl-2-pentynyl, 4-methyl-2-pentynyl, 1-methyl-3-pentynyl, 2-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-4-pentynyl, 3-methyl-4-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl, and 1-ethyl-1-methyl-2-propynyl. Alkynyl substituents may be unsubstituted or substituted with one or more chemical moieties. Examples of suitable substituents include, for example, hydroxy, nitro, cyano, formyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₁-C₆ acyl, C₁-C₆ alkylthio, C₁-C₆ haloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆ haloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ haloalkoxycarbonyl, C₁-C₆ carbamoyl, C₁-C₆ halocarbamoyl, hydroxycarbonyl, C₁-C₆ alkylcarbonyl, C₁-C₆ haloalkylcarbonyl, aminocarbonyl, C₁-C₆ alkylaminocarbonyl, haloalkylaminocarbonyl, C₁-C₆ dialkylaminocarbonyl, and C₁-C₆ dihaloalkylaminocarbonyl, provided that the substituents are sterically compatible and the rules of chemical bonding and strain energy are satisfied. Preferred substituents include cyano and C₁-C₆ alkoxy.

As used herein, the term “alkoxy” refers to a group of the formula R—O—, where R is unsubstituted or substituted alkyl as defined above. Unless otherwise specified, alkoxy groups wherein R is a C₁-C₂₀ (e.g., C₁-C₁₂, C₁-C₁₀, C₁-C₈, C₁-C₆, C₁-C₄) alkyl group are intended. Examples include methoxy, ethoxy, propoxy, 1-methyl-ethoxy, butoxy, 1-methyl-propoxy, 2-methyl-propoxy, 1,1-dimethyl-ethoxy, pentoxy, 1-methyl-butyloxy, 2-methyl-butoxy, 3-methyl-butoxy, 2,2-dimethyl-propoxy, 1-ethyl-propoxy, hexoxy, 1,1-dimethyl-propoxy, 1,2-dimethyl-propoxy, 1-methyl-pentoxy, 2-methyl-pentoxy, 3-methyl-pentoxy, 4-methyl-penoxy, 1,1-dimethyl-butoxy, 1,2-dimethyl-butoxy, 1,3-dimethyl-butoxy, 2,2-dimethyl-butoxy, 2,3-dimethyl-butoxy, 3,3-dimethyl-butoxy, 1-ethyl-butoxy, 2-ethylbutoxy, 1,1,2-trimethyl-propoxy, 1,2,2-trimethyl-propoxy, 1-ethyl-1-methyl-propoxy, and 1-ethyl-2-methyl-propoxy.

As used herein, the term “haloalkoxy” refers to a group of the formula R—O—, where R is unsubstituted or substituted haloalkyl as defined above. Unless otherwise specified, haloalkoxy groups wherein R is a C₁-C₂₀ (e.g., C₁-C₁₂, C₁-C₁₀, C₁-C₈, C₁-C₆, C₁-C₄) alkyl group are intended. Examples include chloromethoxy, bromomethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 1-chloroethoxy, 1-bromoethoxy, 1-fluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy, and 1,1,1-trifluoroprop-2-oxy.

As used herein, the term “alkylthio” refers to a group of the formula R—S—, where R is unsubstituted or substituted alkyl as defined above. Unless otherwise specified, alkylthio groups wherein R is a C₁-C₂₀ (e.g., C₁-C₁₂, C₁-C₁₀, C₁-C₈, C₁-C₆, C₁-C₄) alkyl group are intended. Examples include methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methyl-propylthio, 2-methylpropylthio, 1,1-dimethylethylthio, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2,2-do-methylpropylthio, 1-ethylpropylthio, hexylthio, 1,1-dimethylpropylthio, 1,2-dimethyl propylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methyl-pentylthio, 4-methyl-pentylthio, 1,1-dimethyl butylthio, 1,2-dimethyl-butylthio, 1,3-dimethyl-butylthio, 2,2-dimethyl butylthio, 2,3-dimethyl butylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio, 1,1,2-trimethyl propylthio, 1,2,2-trimethyl propylthio, 1-ethyl-1-methyl propylthio, and 1-ethyl-2-methylpropylthio.

As used herein, the term “haloalkylthio” refers to an alkylthio group as defined above wherein the carbon atoms are partially or entirely substituted with halogen atoms. Unless otherwise specified, haloalkylthio groups wherein R is a C₁-C₂₀ (e.g., C₁-C₁₂, C₁-C₁₀, C₁-C₈, C₁-C₆, C₁-C₄) alkyl group are intended. Examples include chloromethylthio, bromomethylthio, dichloromethylthio, trichloromethylthio, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorofluoromethylthio, dichlorofluoro-methylthio, chlorodifluoromethylthio, 1-chloroethylthio, 1-bromoethylthio, 1-fluoroethylthio, 2-fluoroethylthio, 2,2-difluoroethylthio, 2,2,2-trifluoroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro-2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, 2,2,2-trichloroethylthio, pentafluoroethylthio, and 1,1,1-trifluoroprop-2-ylthio.

As used herein, the term “aryl,” as well as derivative terms such as aryloxy, refers to groups that include a monovalent aromatic carbocyclic group of from 6 to 14 carbon atoms. Aryl groups can include a single ring or multiple condensed rings. In some embodiments, aryl groups include C₆-C₁₀ aryl groups. Examples of aryl groups include, but are not limited to, phenyl, biphenyl, naphthyl, tetrahydronaphthyl, phenylcyclopropyl, and indanyl. In some embodiments, the aryl group can be a phenyl, indanyl or naphthyl group. The term “heteroaryl”, as well as derivative terms such as “heteroaryloxy”, refers to a 5- or 6-membered aromatic ring containing one or more heteroatoms, viz., N, O or S; these heteroaromatic rings may be fused to other aromatic systems. The aryl or heteroaryl substituents may be unsubstituted or substituted with one or more chemical moieties. Examples of suitable substituents include, for example, hydroxy, halogen, nitro, cyano, formyl, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₁-C₆ alkoxy, C₁-C₆ haloalkyl, C₁-C₆ haloalkoxy, C₁-C₆ acyl, C₁-C₆ alkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ carbamoyl, hydroxycarbonyl, C₁-C₆ alkylcarbonyl, aminocarbonyl, C₁-C₆ alkylaminocarbonyl, C₁-C₆ dialkylaminocarbonyl, provided that the substituents are sterically compatible and the rules of chemical bonding and strain energy are satisfied. Preferred substituents include halogen, C₁-C₂ alkyl and C₁-C₂ haloalkyl.

As used herein, the term “alkylcarbonyl” refers to an unsubstituted or substituted alkyl group bonded to a carbonyl group. C₁-C₃ alkylcarbonyl and C₁-C₃ haloalkylcarbonyl refer to groups wherein a C₁-C₃ unsubstituted or substituted alkyl or haloalkyl group is bonded to a carbonyl group (the group contains a total of 2 to 4 carbon atoms).

As used herein, the term “alkoxycarbonyl” refers to a group of the formula

wherein R is unsubstituted or substituted alkyl.

As used herein, the term “arylalkyl” refers to an alkyl group substituted with an unsubstituted or substituted aryl group. C₇-C₁₀ arylalkyl refers to a group wherein the total number of carbon atoms in the group is 7 to 10, not including the carbon atoms present in any substituents of the aryl group.

As used herein, the term “alkylamino” refers to an amino group substituted with one or two unsubstituted or substituted alkyl groups, which may be the same or different.

As used herein, the term “haloalkylamino” refers to an alkylamino group wherein the alkyl carbon atoms are partially or entirely substituted with halogen atoms.

As used herein, C₁-C₆ alkylaminocarbonyl refers to a group of the formula RNHC(O)— wherein R is C₁-C₆ unsubstituted or substituted alkyl, and C₁-C₆ dialkylaminocarbonyl refers to a group of the formula R₂NC(O)— wherein each R is independently C₁-C₆ unsubstituted or substituted alkyl.

As used herein, the term “alkylcarbamyl” refers to a carbamyl group substituted on the nitrogen with an unsubstituted or substituted alkyl group.

As used herein, the term “alkylsulfonyl” refers to a group of the formula

where R is unsubstituted or substituted alkyl.

As used herein, the term “carbamyl” (also referred to as carbamoyl and aminocarbonyl) refers to a group of the formula

As used herein, the term “dialkylphosphonyl” refers to a group of the formula

where R is independently unsubstituted or substituted alkyl in each occurrence.

As used herein, C₁-C₆ trialkylsilyl refers to a group of the formula —SiR₃ wherein each R is independently a C₁-C₆ unsubstituted or substituted alkyl group (the group contains a total of 3 to 18 carbon atoms).

As used herein, Me refers to a methyl group; OMe refers to a methoxy group; and i-Pr refers to an isopropyl group.

As used herein, the term “halogen” including derivative terms such as “halo” refers to fluorine, chlorine, bromine and iodine.

As used herein, agriculturally acceptable salts and esters refer to salts and esters that exhibit herbicidal activity, or that are or can be converted in plants, water, or soil to the referenced herbicide. Exemplary agriculturally acceptable esters are those that are or can by hydrolyzed, oxidized, metabolized, or otherwise converted, e.g., in plants, water, or soil, to the corresponding carboxylic acid which, depending on the pH, may be in the dissociated or undissociated form.

Compounds described herein can include N-oxides. Pyridine N-oxides can be obtained by oxidation of the corresponding pyridines. Suitable oxidation methods are described, for example, in Houben-Weyl, Methoden der organischen Chemie [Methods in organic chemistry], expanded and subsequent volumes to the 4th edition, volume E 7b, p. 565 f.

Pyridine Carboxylic Acid Herbicides

Compositions and methods of the present disclosure can include a pyridine carboxylic acid herbicide defined by Formula (I)

wherein

X is N or CY, wherein Y is hydrogen, halogen, C₁-C₃ alkyl, C₁-C₃ haloalkyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio or C₁-C₃ haloalkylthio;

R¹ is OR^(1′) or NR^(1″)R^(1″′), wherein R^(1′) is hydrogen, C₁-C₈ alkyl, C₁-C₆ haloalkyl, or C₇-C₁₀ arylalkyl, and R^(1″) and R^(1″′) are independently hydrogen, C₁-C₁₂ alkyl, C₃-C₁₂ alkenyl, or C₃-C₁₂ alkynyl;

R² is hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄ haloalkylamino, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, cyano, or a group of the formula —CR¹⁷═CR¹⁸—SiR¹⁹R²⁰R²¹, wherein R¹⁷ is hydrogen, F, or Cl; R¹⁸ is hydrogen, F, Cl, C₁-C₄ alkyl, or C₁-C₄ haloalkyl; and R¹⁹, R²⁰, and R²¹ are independently C₁-C₁₀ alkyl, C₃-C₆ cycloalkyl, phenyl, substituted phenyl, C₁-C₁₀ alkoxy, or OH;

R³ and R⁴ are independently hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆ alkylsulfonyl, C₁-C₆ trialkylsilyl, C₁-C₆ dialkylphosphonyl, or R³ and R⁴ taken together with N is a 5- or 6-membered saturated ring, or R³ and R⁴ taken together represent ═CR^(3′)(R^(4′)), wherein R^(3′) and R^(4′) are independently hydrogen, C₁-C₆ alkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl, C₁-C₆ alkoxy or C₁-C₆ alkylamino, or, R^(3′) and R^(4′) taken together with ═C represent a 5- or 6-membered saturated ring;

A is one of groups A1 to A36

R⁵, if applicable to the A group, is hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄ haloalkylamino, OH, or CN;

R⁶, R^(6′), and R⁶″, if applicable to the A group, are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino or C₂-C₄ haloalkylamino, OH, CN, or NO₂;

R⁷ and R^(7′) are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, C₁-C₄ haloalkylamino, or phenyl;

R⁸ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆ alkylsulfonyl, C₁-C₆ trialkylsilyl, or phenyl;

or an agriculturally acceptable N-oxide or salt thereof.

In some embodiments, R¹ is OR^(1′), wherein R^(1′) is hydrogen, C₁-C₈ alkyl, or C₇-C₁₀ arylalkyl. In some embodiments, R^(1′) is hydrogen or C₁-C₈ alkyl. In some embodiments, R^(1′) is hydrogen.

In some embodiments, R² is halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkynyl, C₂-C₄-alkenyl, C₂-C₄ haloalkenyl, C₁-C₄-alkoxy, or C₁-C₄ haloalkoxy. In some embodiments, R² is halogen, C₂-C₄-alkenyl, C₂-C₄ haloalkenyl, or C₁-C₄-alkoxy. In some embodiments, R² is halogen. In some embodiments, R² is C₂-C₄-alkenyl or C₂-C₄ haloalkenyl. In some embodiments, R² is C₁-C₄ alkoxy. In some embodiments, R² is Cl, OMe, vinyl, or 1-propenyl. In some embodiments, R² is C₁. In some embodiments, R² is OMe. In some embodiments, R² is vinyl or 1-propenyl.

In some embodiments, R³ and R⁴ are independently hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbamyl, or R³ and R⁴ taken together represent ═CR^(3′)(R^(4′)), wherein R^(3′) and R^(4′) are independently hydrogen, C₁-C₆ alkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl, C₁-C₆ alkoxy, or C₁-C₆ alkylamino. In some embodiments, R³ and R⁴ are independently hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, or R³ and R⁴ taken together represent ═CR^(3′)(R^(4′)), wherein R^(3′) and R^(4′) are independently hydrogen, C₁-C₆ alkyl, C₁-C₆ alkoxy or C₁-C₆ alkylamino.

In some embodiments, R³ and R⁴ are independently hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, formyl, C₁-C₃ alkylcarbonyl, or C₁-C₃ haloalkylcarbonyl. In some embodiments, at least one of R³ and R⁴ are hydrogen. In some embodiments, R³ and R⁴ are both hydrogen.

In some embodiments, X is N, CH or CF. In some embodiments, X is N. In some embodiments, X is CH. In some embodiments, X is CF. In other embodiments, X is C—CH₃.

In some embodiments, A is A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15, A16, A17, A18, A19, or A20. In other embodiments, A is one of A21, A22, A23, A24, A25, A26, A27, A28, A29, A30, A31, A32, A33, A34, A35, and A36.

In some embodiments, A is A1, A2, A3, A7, A8, A9, A10, A11, A12, A13, A14, or A15. In some embodiments, A is one of groups A1, A2, A3, A7, A8, A9, A10, A13, A14, and A15. In some embodiments, A is one of groups A1, A2, A3, A13, A14, and A15. In certain cases, A is A2, A3, A8, A13, or A15. In some embodiments, A is one of groups A13, A14, and A15. In some embodiments, A is A15.

In some embodiments, R⁵ is hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, or amino. In some embodiments, R⁵ is hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, or amino. In some embodiments, R⁵ is hydrogen, halogen, C₁-C₄ alkyl or C₁-C₄ alkoxy. In some embodiments, R⁵ is hydrogen or F. In some embodiments, R⁵ is hydrogen.

In other embodiments, R⁵ is F.

In some embodiments, R⁶ is hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₁-C₃ alkoxy, or C₁-C₃ haloalkoxy. In some embodiments, R⁶ is hydrogen or fluorine. In some embodiments, R⁶ is hydrogen. In some embodiments, R⁶ is fluorine.

In some embodiments, R^(6′) is hydrogen or halogen. In some embodiments, R^(6′) is hydrogen, F, or C₁. In some embodiments, R^(6′) is hydrogen or F. In some embodiments, R^(6′) is hydrogen.

In some embodiments, R⁶″ is hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl, C₂-C₄ alkynyl, CN, or NO₂. In some embodiments, R⁶″ is hydrogen. In some embodiments, R⁶″ is halogen. In some embodiments, R⁶″ is C₁-C₄ alkyl. In some embodiments, R⁶″ is C₁-C₄ haloalkyl. In some embodiments, R⁶″ is cyclopropyl. In some embodiments, R⁶″ is C₂-C₄ alkynyl. In some embodiments, R⁶″ is CN. In some embodiments, R⁶″ is NO₂.

In some embodiments:

X is N, CH, CF, CCl, or CBr;

R¹ is OR^(1′), wherein R^(1′) is hydrogen or C₁-C₄ alkyl;

R² is chlorine;

R³ and R⁴ are hydrogen;

A is A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15, A16, A17, A18, A19, or A20;

R⁵ is hydrogen, halogen, OH, amino, CN, C₁-C₃ alkyl, C₁-C₃ alkoxy, C₁-C₃ alkylamino, or cyclopropyl;

R⁶, R^(6′), and R⁶″ are independently hydrogen, halogen, OH, NH₂, CN, C₁-C₃ alkyl, C₁-C₃ alkoxy, cyclopropyl, or vinyl;

R⁷ and R^(7′) are independently hydrogen, halogen, C₁-C₃ alkyl, C₁-C₃ alkoxy, C₁-C₃ alkylthio, cyclopropyl, C₁-C₃ alkylamino, or phenyl; and

R⁸ is hydrogen, C₁-C₃ alkyl, phenyl, or C₁-C₃ alkylcarbonyl.

In some embodiments, R² is halogen, C₂-C₄-alkenyl, C₂-C₄ haloalkenyl, or C₁-C₄-alkoxy;

R³ and R⁴ are both hydrogen; and X is N, CH, or CF.

In some embodiments, R² is halogen; R³ and R⁴ are both hydrogen; and X is N, CH, or CF.

In some embodiments, R² is C₂-C₄-alkenyl or C₂-C₄ haloalkenyl; R³ and R⁴ are both hydrogen; and X is N, CH, or CF.

In some embodiments, R² is C₁-C₄-alkoxy; R³ and R⁴ are both hydrogen; and X is N, CH, or CF.

In some embodiments, R² is halogen, C₂-C₄-alkenyl, C₂-C₄ haloalkenyl, or C₁-C₄-alkoxy;

R³ and R⁴ are both hydrogen; X is N, CH, or CF; R⁵ is hydrogen or F; R⁶ is hydrogen or F; R^(6′) is hydrogen; R⁶″, if applicable to the relevant A group, is hydrogen or halogen; and R⁷ and R^(7′), if applicable to the relevant A group, are independently hydrogen or halogen.

In some embodiments, R² is halogen, C₁-C₄-alkoxy, or C₂-C₄-alkenyl; R³ and R⁴ are hydrogen; X is N, CH, or CF; and A is one of groups A1 to A20.

In some embodiments, R² is chlorine; R³ and R⁴ are hydrogen; X is N, CH, or CF; A is one of groups A1 to A20; R⁵ is hydrogen or F; R⁶ and R^(6′) are independently hydrogen or F; and

R⁷ and R^(7′), if applicable to the relevant A group, are independently hydrogen, halogen, C₁-C₄ alkyl, or C₁-C₄ haloalkyl.

In some embodiments, R² is chlorine, methoxy, vinyl, or 1-propenyl; R³ and R⁴ are hydrogen; and X is N, CH, or CF.

In some embodiments, R² is chlorine; R³ and R⁴ are hydrogen; and X is N, CH, or CF.

In some embodiments, R² is vinyl or 1-propenyl; R³ and R⁴ are hydrogen; and X is N, CH, or CF.

In some embodiments, R² is methoxy; R³ and R⁴ are hydrogen; and X is N, CH, or CF.

In some embodiments, R² is chlorine; R³ and R⁴ are hydrogen; and X is N.

In some embodiments, R² is chlorine; R³ and R⁴ are hydrogen; and X is CH.

In some embodiments, R² is chlorine; R³ and R⁴ are hydrogen; and X is CF.

In some embodiments, R² is chlorine; R³ and R⁴ are hydrogen; X is CF; A is one of A1, A2, A3, A7, A8, A9, A10, A13, A14, or A15; R⁵ is F; and R⁶ is H.

In some embodiments, R² is chlorine, methoxy, vinyl, or 1-propenyl; R³ and R⁴ are hydrogen; X is N, CH, or CF; and A is one of A21 to A36.

In some embodiments, R² is chlorine, methoxy, vinyl, or 1-propenyl; R³ and R⁴ are hydrogen; X is CF; and A is one of

wherein R⁵ is hydrogen or F.

In some embodiments, R² is chlorine, methoxy, vinyl, or 1-propenyl; R³ and R⁴ are hydrogen; X is N, CH, or CF; and A is

where R⁵ is hydrogen or F.

In some embodiments, R² is chlorine, methoxy, vinyl, or 1-propenyl; R³ and R⁴ are hydrogen; X is N, CH, or CF; and A is

In some embodiments, R² is chlorine, methoxy, vinyl, or 1-propenyl; R³ and R⁴ are hydrogen; X is CF; and A is

In some embodiments, the pyridine carboxylic acid herbicide can comprise a compound defined by Formula (I)

wherein

X is N or CY, wherein Y is hydrogen, halogen, C₁-C₃ alkyl, C₁-C₃ haloalkyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, or C₁-C₃ haloalkylthio;

R¹ is OR^(1′) or NR^(1″)R^(1″′), wherein R^(1′) is hydrogen, C₁-C₈ alkyl, C₁-C₈ haloalkyl, or C₇-C₁₀ arylalkyl, and R^(1″) and R^(1″′) are independently hydrogen, C₁-C₁₂ alkyl, C₃-C₁₂ alkenyl, or C₃-C₁₂ alkynyl;

R² is hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄ haloalkylamino, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, cyano, or a group of the formula —CR¹⁷═CR¹⁸—SiR¹⁹R²⁰R²¹, wherein R¹⁷ is hydrogen, F, or Cl; R¹⁸ is hydrogen, F, Cl, C₁-C₄ alkyl, or C₁-C₄ haloalkyl; and R¹⁹, R²⁰, and R²¹ are independently C₁-C₁₀ alkyl, C₃-C₆ cycloalkyl, phenyl, substituted phenyl, C₁-C₁₀ alkoxy, or OH;

R³ and R⁴ are independently hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆ alkylsulfonyl, C₁-C₆ trialkylsilyl, C₁-C₆ dialkylphosphonyl, or R³ and R⁴ taken together with N is a 5- or 6-membered saturated ring, or R³ and R⁴ taken together represent ═CR^(3′)(R^(4′)), wherein R^(3′) and R^(4′) are independently hydrogen, C₁-C₆ alkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl, C₁-C₆ alkoxy or C₁-C₆ alkylamino, or, R^(3′) and R^(4′) taken together with ═C represent a 5- or 6-membered saturated ring;

A is A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15, A16, A17, A18, A19, A20, A21, A22, A23, A24, A25, A26, A27, A28, A29, A30, A31, A32, A33, A34, A35, or A36;

R⁵ is hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄ haloalkylamino, OH, or CN;

R⁶, R^(6′), and R⁶″ are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino or C₂-C₄ haloalkylamino, OH, CN, or NO₂;

R⁷ and R^(7′) are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄ haloalkylamino, or phenyl; and

R⁸ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆ alkylsulfonyl, C₁-C₆ trialkylsilyl, or phenyl;

or an agriculturally acceptable N-oxide or salt thereof,

with the proviso that the pyridine carboxylic acid herbicide is not a compound defined by Formula (I)

wherein

X is N, CH, CF, CCl, or CBr;

R¹ is OR^(1′), wherein R^(1′) is hydrogen or C₁-C₄ alkyl;

R² is chlorine;

R³ and R⁴ are hydrogen;

A is A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15, A16, A17, A18, A19, or A20;

R⁵ is hydrogen, halogen, OH, amino, CN, C₁-C₃ alkyl, C₁-C₃ alkoxy, C₁-C₃ alkylamino, or cyclopropyl;

R⁶, R^(6′), and R⁶″ are independently hydrogen, halogen, OH, NH₂, CN, C₁-C₃ alkyl, C₁-C₃ alkoxy, cyclopropyl, or vinyl;

R⁷ and R^(7′) are independently hydrogen, halogen, C₁-C₃ alkyl, C₁-C₃ alkoxy, C₁-C₃ alkylthio, cyclopropyl, C₁-C₃ alkylamino, or phenyl; and

R⁸ is hydrogen, C₁-C₃ alkyl, phenyl, or C₁-C₃ alkylcarbonyl;

or an agriculturally acceptable N-oxide or salt thereof.

In some of these embodiments, R¹ is OR¹. In some of these embodiments, X is CF. In some of these embodiments, A is A15. In some of these embodiments, R⁵ is F.

In some embodiments:

X is CY, wherein Y is C₁-C₃ alkyl, C₁-C₃ haloalkyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, or C₁-C₃ haloalkylthio;

R¹ is OR^(1′) or NR^(1″)R^(1″′), wherein R^(1′) is hydrogen, C₁-C₈ alkyl, or C₇-C₁₀ arylalkyl, and R^(1″) and R^(1″′) are independently hydrogen, C₁-C₁₂ alkyl, C₃-C₁₂ alkenyl, or C₃-C₁₂ alkynyl;

R² is halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄ haloalkylamino, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, cyano, or a group of the formula —CR¹⁷═CR¹⁸—SiR¹⁹R²⁰R²¹, wherein R¹⁷ is hydrogen, F, or Cl; R¹⁸ is hydrogen, F, Cl, C₁-C₄ alkyl, or C₁-C₄ haloalkyl; and R¹⁹, R²⁰, and R²¹ are independently C₁-C₁₀ alkyl, C₃-C₆ cycloalkyl, phenyl, substituted phenyl, C₁-C₁₀ alkoxy, or OH;

R³ and R⁴ are independently hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆ alkylsulfonyl, C₁-C₆ trialkylsilyl, C₁-C₆ dialkylphosphonyl, or R³ and R⁴ taken together with N is a 5- or 6-membered saturated ring, or R³ and R⁴ taken together represent ═CR^(3′)(R^(4′)), wherein R^(3′) and R^(4′) are independently hydrogen, C₁-C₆ alkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl, C₁-C₆ alkoxy or C₁-C₆ alkylamino, or, R^(3′) and R^(4′) taken together with ═C represent a 5- or 6-membered saturated ring;

A is A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15, A16, A17, A18, A19, A20, A21, A22, A23, A24, A25, A26, A27, A28, A29, A30, A31, A32, A33, A34, A35, or A36;

R⁵ is hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄ haloalkylamino, OH, or CN;

R⁶, R^(6′), and R⁶″ are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino or C₂-C₄ haloalkylamino, OH, CN, or NO₂;

R⁷ and R^(7′) are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄ haloalkylamino, or phenyl; and

R⁸ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆ alkylsulfonyl, C₁-C₆ trialkylsilyl, or phenyl.

In some of these embodiments, R¹ is OR¹. In some of these embodiments, A is A15. In some of these embodiments, R⁵ is F.

In some embodiments:

X is N or CY, wherein Y is hydrogen, halogen, C₁-C₃ alkyl, C₁-C₃ haloalkyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, or C₁-C₃ haloalkylthio;

R¹ is OR^(1′) or NR^(1″)R^(1″′), wherein R^(1′) is C₅-C₈ alkyl, or C₇-C₁₀ arylalkyl, and R^(1″) and R^(1″′) are independently hydrogen, C₁-C₁₂ alkyl, C₃-C₁₂ alkenyl, or C₃-C₁₂ alkynyl;

R² is halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄ haloalkylamino, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, cyano, or a group of the formula —CR¹⁷═CR¹⁸—SiR¹⁹R²⁰R²¹, wherein R¹⁷ is hydrogen, F, or Cl; R¹⁸ is hydrogen, F, Cl, C₁-C₄ alkyl, or C₁-C₄ haloalkyl; and R¹⁹, R²⁰, and R²¹ are independently C₁-C₁₀ alkyl, C₃-C₆ cycloalkyl, phenyl, substituted phenyl, C₁-C₁₀ alkoxy, or OH;

R³ and R⁴ are independently hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆ alkylsulfonyl, C₁-C₆ trialkylsilyl, C₁-C₆ dialkylphosphonyl, or R³ and R⁴ taken together with N is a 5- or 6-membered saturated ring, or R³ and R⁴ taken together represent ═CR^(3′)(R^(4′)), wherein R^(3′) and R^(4′) are independently hydrogen, C₁-C₆ alkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl, C₁-C₆ alkoxy or C₁-C₆ alkylamino, or, R^(3′) and R^(4′) taken together with ═C represent a 5- or 6-membered saturated ring;

A is A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15, A16, A17, A18, A19, A20, A21, A22, A23, A24, A25, A26, A27, A28, A29, A30, A31, A32, A33, A34, A35, or A36;

R⁵ is hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄ haloalkylamino, OH, or CN;

R⁶, R^(6′), and R⁶″ are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino or C₂-C₄ haloalkylamino, OH, CN, or NO₂;

R⁷ and R^(7′) are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄ haloalkylamino, or phenyl;

R⁸ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆ alkylsulfonyl, C₁-C₆ trialkylsilyl, or phenyl; In some of these embodiments, R¹ is OR¹. In some of these embodiments, X is CF. In some of these embodiments, A is A15. In some of these embodiments, R⁵ is F.

In some embodiments:

X is N or CY, wherein Y is hydrogen, halogen, C₁-C₃ alkyl, C₁-C₃ haloalkyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, or C₁-C₃ haloalkylthio;

R¹ is OR^(1′) or NR^(1″)R^(1″′), wherein R^(1′) is hydrogen, C₁-C₈ alkyl, or C₇-C₁₀ arylalkyl, and R^(1″) and R^(1″′) are independently hydrogen, C₁-C₁₂ alkyl, C₃-C₁₂ alkenyl, or C₃-C₁₂ alkynyl;

R² is F, Br, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄ haloalkylamino, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, cyano, or a group of the formula —CR¹⁷═CR¹⁸—SiR¹⁹R²⁰R²¹, wherein R¹⁷ is hydrogen, F, or Cl; R¹⁸ is hydrogen, F, Cl, C₁-C₄ alkyl, or C₁-C₄ haloalkyl; and R¹⁹, R²⁰, and R²¹ are independently C₁-C₁₀ alkyl, C₃-C₆ cycloalkyl, phenyl, substituted phenyl, C₁-C₁₀ alkoxy, or OH;

R³ and R⁴ are independently hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆ alkylsulfonyl, C₁-C₆ trialkylsilyl, C₁-C₆ dialkylphosphonyl, or R³ and R⁴ taken together with N is a 5- or 6-membered saturated ring, or R³ and R⁴ taken together represent ═CR^(3′)(R^(4′)), wherein R^(3′) and R^(4′) are independently hydrogen, C₁-C₆ alkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl, C₁-C₆ alkoxy or C₁-C₆ alkylamino, or, R^(3′) and R^(4′) taken together with ═C represent a 5- or 6-membered saturated ring;

A is A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15, A16, A17, A18, A19, A20, A21, A22, A23, A24, A25, A26, A27, A28, A29, A30, A31, A32, A33, A34, A35, or A36;

R⁵ is hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄ haloalkylamino, OH, or CN;

R⁶, R^(6′), and R⁶″ are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino or C₂-C₄ haloalkylamino, OH, CN, or NO₂;

R⁷ and R^(7′) are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄ haloalkylamino, or phenyl; and

R⁸ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆ alkylsulfonyl, C₁-C₆ trialkylsilyl, or phenyl.

In some of these embodiments, R¹ is OR¹. In some of these embodiments, X is CF. In some of these embodiments, A is A15. In some of these embodiments, R⁵ is F.

In some embodiments:

X is N or CY, wherein Y is hydrogen, halogen, C₁-C₃ alkyl, C₁-C₃ haloalkyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, or C₁-C₃ haloalkylthio;

R¹ is OR^(1′) or NR^(1″)R^(1″′), wherein R^(1′) is hydrogen, C₁-C₈ alkyl, or C₇-C₁₀ arylalkyl, and R^(1″) and R^(1″′) are independently hydrogen, C₁-C₁₂ alkyl, C₃-C₁₂ alkenyl, or C₃-C₁₂ alkynyl;

R² is halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄ haloalkylamino, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, cyano, or a group of the formula —CR¹⁷═CR¹⁸—SiR¹⁹R²⁰R²¹, wherein R¹⁷ is hydrogen, F, or Cl; R¹⁸ is hydrogen, F, Cl, C₁-C₄ alkyl, or C₁-C₄ haloalkyl; and R¹⁹, R²⁰, and R²¹ are independently C₁-C₁₀ alkyl, C₃-C₆ cycloalkyl, phenyl, substituted phenyl, C₁-C₁₀ alkoxy, or OH;

R³ and R⁴ are independently C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆ alkylsulfonyl, C₁-C₆ trialkylsilyl, C₁-C₆ dialkylphosphonyl, or R³ and R⁴ taken together with N is a 5- or 6-membered saturated ring, or R³ and R⁴ taken together represent ═CR^(3′)(R^(4′)), wherein R^(3′) and R^(4′) are independently hydrogen, C₁-C₆ alkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl, C₁-C₆ alkoxy or C₁-C₆ alkylamino, or, R^(3′) and R^(4′) taken together with ═C represent a 5- or 6-membered saturated ring;

A is A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15, A16, A17, A18, A19, A20, A21, A22, A23, A24, A25, A26, A27, A28, A29, A30, A31, A32, A33, A34, A35, or A36;

R⁵ is hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄ haloalkylamino, OH, or CN;

R⁶, R^(6′), and R⁶″ are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino or C₂-C₄ haloalkylamino, OH, CN, or NO₂;

R⁷ and R^(7′) are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄ haloalkylamino, or phenyl; and

R⁸ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆ alkylsulfonyl, C₁-C₆ trialkylsilyl, or phenyl.

In some of these embodiments, R¹ is OR¹. In some of these embodiments, X is CF. In some of these embodiments, A is A15. In some of these embodiments, R⁵ is F.

In some embodiments:

X is N or CY, wherein Y is hydrogen, halogen, C₁-C₃ alkyl, C₁-C₃ haloalkyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, or C₁-C₃ haloalkylthio;

R¹ is OR^(1′) or NR^(1″)R^(1″′), wherein R^(1′) is hydrogen, C₁-C₈ alkyl, or C₇-C₁₀ arylalkyl, and R^(1″) and R^(1″′) are independently hydrogen, C₁-C₁₂ alkyl, C₃-C₁₂ alkenyl, or C₃-C₁₂ alkynyl;

R² is halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄ haloalkylamino, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, cyano, or a group of the formula —CR¹⁷═CR¹⁸—SiR¹⁹R²⁰R²¹, wherein R¹⁷ is hydrogen, F, or Cl; R¹⁸ is hydrogen, F, Cl, C₁-C₄ alkyl, or C₁-C₄ haloalkyl; and R¹⁹, R²⁰, and R²¹ are independently C₁-C₁₀ alkyl, C₃-C₆ cycloalkyl, phenyl, substituted phenyl, C₁-C₁₀ alkoxy, or OH;

R³ and R⁴ are independently hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆ alkylsulfonyl, C₁-C₆ trialkylsilyl, C₁-C₆ dialkylphosphonyl, or R³ and R⁴ taken together with N is a 5- or 6-membered saturated ring, or R³ and R⁴ taken together represent ═CR^(3′)(R^(4′)), wherein R^(3′) and R^(4′) are independently hydrogen, C₁-C₆ alkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl, C₁-C₆ alkoxy or C₁-C₆ alkylamino, or, R^(3′) and R^(4′) taken together with ═C represent a 5- or 6-membered saturated ring;

A is A21, A22, A23, A24, A25, A26, A27, A28, A29, A30, A31, A32, A33, A34, A35, or A36;

R⁵ is hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄ haloalkylamino, OH, or CN;

R⁶, R^(6′), and R⁶″ are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino or C₂-C₄ haloalkylamino, OH, CN, or NO₂;

R⁷ and R^(7′) are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄ haloalkylamino, or phenyl; and

R⁸ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆ alkylsulfonyl, C₁-C₆ trialkylsilyl, or phenyl.

In some of these embodiments, R¹ is OR¹. In some of these embodiments, X is CF. In some of these embodiments, R⁵ is F.

In some embodiments:

X is N or CY, wherein Y is hydrogen, halogen, C₁-C₃ alkyl, C₁-C₃ haloalkyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, or C₁-C₃ haloalkylthio;

R¹ is OR^(1′) or NR^(1″)R^(1″′), wherein R^(1′) is hydrogen, C₁-C₈ alkyl, or C₇-C₁₀ arylalkyl, and R^(1″) and R^(1″′) are independently hydrogen, C₁-C₁₂ alkyl, C₃-C₁₂ alkenyl, or C₃-C₁₂ alkynyl;

R² is halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄ haloalkylamino, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, cyano, or a group of the formula —CR¹⁷═CR¹⁸—SiR¹⁹R²⁰R²¹, wherein R¹⁷ is hydrogen, F, or Cl; R¹⁸ is hydrogen, F, Cl, C₁-C₄ alkyl, or C₁-C₄ haloalkyl; and R¹⁹, R²⁰, and R²¹ are independently C₁-C₁₀ alkyl, C₃-C₆ cycloalkyl, phenyl, substituted phenyl, C₁-C₁₀ alkoxy, or OH;

R³ and R⁴ are independently hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆ alkylsulfonyl, C₁-C₆ trialkylsilyl, C₁-C₆ dialkylphosphonyl, or R³ and R⁴ taken together with N is a 5- or 6-membered saturated ring, or R³ and R⁴ taken together represent ═CR^(3′)(R^(4′)), wherein R^(3′) and R^(4′) are independently hydrogen, C₁-C₆ alkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl, C₁-C₆ alkoxy or C₁-C₆ alkylamino, or, R^(3′) and R^(4′) taken together with ═C represent a 5- or 6-membered saturated ring;

A is A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15, A16, A17, A18, A19, or A20;

R⁵ is C₁-C₄ alkyl, C₁-C₄ haloalkyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, C₁-C₄ alkylamino, or C₂-C₄ haloalkylamino;

R⁶, R^(6′), and R⁶″ are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino or C₂-C₄ haloalkylamino, OH, CN, or NO₂;

R⁷ and R^(7′) are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄ haloalkylamino, or phenyl; and

R⁸ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆ alkylsulfonyl, C₁-C₆ trialkylsilyl, or phenyl.

In some of these embodiments, R¹ is OR¹. In some of these embodiments, X is CF. In some of these embodiments, A is A15. In some of these embodiments, R⁵ is F.

In some embodiments:

X is N or CY, wherein Y is hydrogen, halogen, C₁-C₃ alkyl, C₁-C₃ haloalkyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, or C₁-C₃ haloalkylthio;

R¹ is OR^(1′) or NR^(1″)R^(1″′), wherein R^(1′) is hydrogen, C₁-C₈ alkyl, or C₇-C₁₀ arylalkyl, and R^(1″) and R^(1″′) are independently hydrogen, C₁-C₁₂ alkyl, C₃-C₁₂ alkenyl, or C₃-C₁₂ alkynyl;

R² is halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄ haloalkylamino, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, cyano, or a group of the formula —CR¹⁷═CR¹⁸—SiR¹⁹R²⁰R²¹, wherein R¹⁷ is hydrogen, F, or Cl; R¹⁸ is hydrogen, F, Cl, C₁-C₄ alkyl, or C₁-C₄ haloalkyl; and R¹⁹, R²⁰, and R²¹ are independently C₁-C₁₀ alkyl, C₃-C₆ cycloalkyl, phenyl, substituted phenyl, C₁-C₁₀ alkoxy, or OH;

R³ and R⁴ are independently hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆ alkylsulfonyl, C₁-C₆ trialkylsilyl, C₁-C₆ dialkylphosphonyl, or R³ and R⁴ taken together with N is a 5- or 6-membered saturated ring, or R³ and R⁴ taken together represent ═CR^(3′)(R^(4′)), wherein R^(3′) and R^(4′) are independently hydrogen, C₁-C₆ alkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl, C₁-C₆ alkoxy or C₁-C₆ alkylamino, or, R^(3′) and R^(4′) taken together with ═C represent a 5- or 6-membered saturated ring;

A is A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15, A16, A17, A18, A19, or A20;

R⁵ is hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄ haloalkylamino, OH, or CN;

R⁶, R^(6′), and R⁶″ are independently C₁-C₄ alkyl, C₁-C₄ haloalkyl, halocyclopropyl, C₃-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, C₁-C₄ alkylamino or C₂-C₄ haloalkylamino, or NO₂;

R⁷ and R^(7′) are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄ haloalkylamino, or phenyl; and

R⁸ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆ alkylsulfonyl, C₁-C₆ trialkylsilyl, or phenyl.

In some of these embodiments, R¹ is OR¹. In some of these embodiments, X is CF. In some of these embodiments, A is A15. In some of these embodiments, R⁵ is F.

In some embodiments:

X is N or CY, wherein Y is hydrogen, halogen, C₁-C₃ alkyl, C₁-C₃ haloalkyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, or C₁-C₃ haloalkylthio;

R¹ is OR^(1′) or NR^(1″)R^(1″′), wherein R^(1′) is hydrogen, C₁-C₈ alkyl, or C₇-C₁₀ arylalkyl, and R^(1″) and R^(1″′) are independently hydrogen, C₁-C₁₂ alkyl, C₃-C₁₂ alkenyl, or C₃-C₁₂ alkynyl;

R² is halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄ haloalkylamino, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, cyano, or a group of the formula —CR¹⁷═CR¹⁸—SiR¹⁹R²⁰R²¹, wherein R¹⁷ is hydrogen, F, or Cl; R¹⁸ is hydrogen, F, Cl, C₁-C₄ alkyl, or C₁-C₄ haloalkyl; and R¹⁹, R²⁰, and R²¹ are independently C₁-C₁₀ alkyl, C₃-C₆ cycloalkyl, phenyl, substituted phenyl, C₁-C₁₀ alkoxy, or OH;

R³ and R⁴ are independently hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆ alkylsulfonyl, C₁-C₆ trialkylsilyl, C₁-C₆ dialkylphosphonyl, or R³ and R⁴ taken together with N is a 5- or 6-membered saturated ring, or R³ and R⁴ taken together represent ═CR^(3′)(R^(4′)), wherein R^(3′) and R^(4′) are independently hydrogen, C₁-C₆ alkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl, C₁-C₆ alkoxy or C₁-C₆ alkylamino, or, R^(3′) and R^(4′) taken together with ═C represent a 5- or 6-membered saturated ring;

A is A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15, A16, A17, or A18;

R⁵ is hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄ haloalkylamino, OH, or CN;

R⁶, R^(6′), and R⁶″ are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino or C₂-C₄ haloalkylamino, OH, CN, or NO₂;

R⁷ and R^(7′) are independently C₁-C₄ alkyl, C₁-C₄ haloalkyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ haloalkoxy, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, or C₂-C₄ haloalkylamino; and

R⁸ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆ alkylsulfonyl, C₁-C₆ trialkylsilyl, or phenyl

In some of these embodiments, R¹ is OR¹. In some of these embodiments, X is CF. In some of these embodiments, A is A15. In some of these embodiments, R⁵ is F.

In some embodiments:

X is N or CY, wherein Y is hydrogen, halogen, C₁-C₃ alkyl, C₁-C₃ haloalkyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, or C₁-C₃ haloalkylthio;

R¹ is OR^(1′) or NR^(1″)R^(1″′), wherein R^(1′) is hydrogen, C₁-C₈ alkyl, or C₇-C₁₀ arylalkyl, and R^(1″) and R^(1″′) are independently hydrogen, C₁-C₁₂ alkyl, C₃-C₁₂ alkenyl, or C₃-C₁₂ alkynyl;

R² is halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄ haloalkylamino, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, cyano, or a group of the formula —CR¹⁷═CR¹⁸—SiR¹⁹R²⁰R²¹, wherein R¹⁷ is hydrogen, F, or Cl; R¹⁸ is hydrogen, F, Cl, C₁-C₄ alkyl, or C₁-C₄ haloalkyl; and R¹⁹, R²⁰, and R²¹ are independently C₁-C₁₀ alkyl, C₃-C₆ cycloalkyl, phenyl, substituted phenyl, C₁-C₁₀ alkoxy, or OH;

R³ and R⁴ are independently hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆ alkylsulfonyl, C₁-C₆ trialkylsilyl, C₁-C₆ dialkylphosphonyl, or R³ and R⁴ taken together with N is a 5- or 6-membered saturated ring, or R³ and R⁴ taken together represent ═CR^(3′)(R^(4′)), wherein R^(3′) and R^(4′) are independently hydrogen, C₁-C₆ alkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl, C₁-C₆ alkoxy or C₁-C₆ alkylamino, or, R^(3′) and R^(4′) taken together with ═C represent a 5- or 6-membered saturated ring;

A is A3, A6, A11, A12, A15, A18, A19, or A20;

R⁵ is hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄ haloalkylamino, OH, or CN;

R⁶, R^(6′), and R⁶″ are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino or C₂-C₄ haloalkylamino, OH, CN, or NO₂;

R⁷ and R^(7′) are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄ haloalkylamino, or phenyl; and

R⁸ is C₃-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆ alkylsulfonyl, or C₁-C₆ trialkylsilyl.

In some of these embodiments, R¹ is OR¹. In some of these embodiments, X is CF. In some of these embodiments, A is A15. In some of these embodiments, R⁵ is F.

In certain embodiments, the pyridine carboxylic acid herbicide can comprise a compound defined by Formula (II):

wherein

R¹ is OR^(1′) or NR^(1″)R^(1″′), wherein R^(1′) is hydrogen, C₁-C₈ alkyl, C₁-C₆ haloalkyl, or C₇-C₁₀ arylalkyl, and R^(1″) and R^(1″) are independently hydrogen, C₁-C₁₂ alkyl, C₃-C₁₂ alkenyl, or C₃-C₁₂ alkynyl;

R² is hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄ haloalkylamino, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, cyano, or a group of the formula —CR¹⁷═CR¹⁸—SiR¹⁹R²⁰R²¹, wherein R¹⁷ is hydrogen, F, or Cl; R¹⁸ is hydrogen, F, Cl, C₁-C₄ alkyl, or C₁-C₄ haloalkyl; and R¹⁹, R²⁰, and R²¹ are independently C₁-C₁₀ alkyl, C₃-C₆ cycloalkyl, phenyl, substituted phenyl, C₁-C₁₀ alkoxy, or OH;

R³ and R⁴ are independently hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆ alkylsulfonyl, C₁-C₆ trialkylsilyl, C₁-C₆ dialkylphosphonyl, or R³ and R⁴ taken together with N is a 5- or 6-membered saturated ring, or R³ and R⁴ taken together represent ═CR^(3′)(R^(4′)), wherein R^(3′) and R^(4′) are independently hydrogen, C₁-C₆ alkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl, C₁-C₆ alkoxy or C₁-C₆ alkylamino, or, R^(3′) and R^(4′) taken together with ═C represent a 5- or 6-membered saturated ring;

A is A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15, A16, A17, A18, A19, A20, A21, A22, A23, A24, A25, A26, A27, A28, A29, A30, A31, A32, A33, A34, A35, or A36;

R⁵ is hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄ haloalkylamino, OH, or CN;

R⁶, R^(6′), and R⁶″ are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino or C₂-C₄ haloalkylamino, OH, CN, or NO₂;

R⁷ and R^(7′) are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄ haloalkylamino, or phenyl; and

R⁸ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆ alkylsulfonyl, C₁-C₆ trialkylsilyl, or phenyl;

or an agriculturally acceptable N-oxide or salt thereof.

In some embodiments:

R¹ is OR^(1′), wherein R^(1′) is hydrogen, C₁-C₈ alkyl, or C₇-C₁₀ arylalkyl;

R² is halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄-alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₄-alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, or C₁-C₄ haloalkylthio.

R³ and R⁴ are hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, or R³ and R⁴ taken together represent ═CR^(3′)(R^(4′)), wherein R^(3′) and R^(4′) are independently hydrogen, C₁-C₆ alkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl, C₁-C₆ alkoxy or C₁-C₆ alkylamino;

A is A1, A2, A3, A7, A8, A9, A10, A11, A12, A13, A14, A15, A21, A22, A23, A24, A27, A28, A29, A30, A31, or A32;

R⁵ is hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, or C₂-C₄ haloalkylamino;

R⁶, R^(6′), and R⁶″ are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, CN, or NO₂;

R⁷ and R^(7′) are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, cyclopropyl, amino or C₁-C₄ alkylamino; and

R⁸ is hydrogen, C₁-C₆ alkyl, C₁-C₄ haloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, or C₁-C₆ alkylcarbamyl.

In some embodiments, R¹ is OR^(1′), wherein R^(1′) is hydrogen, C₁-C₈ alkyl, or C₇-C₁₀ arylalkyl.

In some embodiments, R² is halogen, C₂-C₄-alkenyl, C₂-C₄ haloalkenyl, or C₁-C₄-alkoxy.

In certain embodiments, R² is Cl, methoxy, vinyl, or 1-propenyl. In some embodiments, R³ and R⁴ are hydrogen.

In some embodiments, A is A1, A2, A3, A7, A8, A9, A10, A13, A14, or A15. In some embodiments, A is A1, A2, A3, A7, A8, A9, A10, A11, A13, A14, or A15. In some embodiments, A is A1, A2, A3, A7, A8, A9, A10, A13, A14, or A15. In certain embodiments, A is A2, A3, A8, A13, or A15. In certain embodiments, A is A1, A2, A3, A13, A14, or A15. In certain embodiments, A is A15.

In some embodiments, R⁵ is hydrogen or F. In certain embodiments, R⁵ is F. In certain embodiments, R⁵ is H.

In some embodiments, R⁶ is hydrogen or F. In certain embodiments, R⁶ is F. In certain embodiments, R⁶ is H. In some embodiments, R⁶″ is hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl, C₂-C₄ alkynyl, CN, or NO₂. In certain embodiments, R⁶, R^(6′), and R⁶″ are all hydrogen.

In certain embodiments, R² is Cl, methoxy, vinyl, or 1-propenyl; R³ and R⁴ are hydrogen;

A is A15; R⁵ is hydrogen or F; R⁶ is hydrogen or F; and R⁶″ is hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl, C₂-C₄ alkynyl, CN, or NO₂.

In certain embodiments, the pyridine carboxylic acid herbicide can comprise a compound defined by Formula (III):

wherein

X is N or CY, wherein Y is hydrogen, halogen, C₁-C₃ alkyl, C₁-C₃ haloalkyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio or C₁-C₃ haloalkylthio;

R¹ is OR^(1′) or NR^(1″)R^(1″′), wherein R^(1′) is hydrogen, C₁-C₈ alkyl, C₁-C₆ haloalkyl, or C₇-C₁₀ arylalkyl, and R^(1″) and R^(1″′) are independently hydrogen, C₁-C₁₂ alkyl, C₃-C₁₂ alkenyl, or C₃-C₁₂ alkynyl;

R² is hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄ haloalkylamino, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, cyano, or a group of the formula —CR¹⁷═CR¹⁸—SiR¹⁹R²⁰R²¹, wherein R¹⁷ is hydrogen, F, or Cl; R¹⁸ is hydrogen, F, Cl, C₁-C₄ alkyl, or C₁-C₄ haloalkyl; and R¹⁹, R²⁰, and R²¹ are independently C₁-C₁₀ alkyl, C₃-C₆ cycloalkyl, phenyl, substituted phenyl, C₁-C₁₀ alkoxy, or OH;

R³ and R⁴ are independently hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆ alkylsulfonyl, C₁-C₆ trialkylsilyl, C₁-C₆ dialkylphosphonyl, or R³ and R⁴ taken together with N is a 5- or 6-membered saturated ring, or R³ and R⁴ taken together represent ═CR^(3′)(R^(4′)), wherein R^(3′) and R^(4′) are independently hydrogen, C₁-C₆ alkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl, C₁-C₆ alkoxy or C₁-C₆ alkylamino, or, R^(3′) and R^(4′) taken together with ═C represent a 5- or 6-membered saturated ring;

R⁶ and R^(6′) are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino or C₂-C₄ haloalkylamino, OH, CN, or NO₂;

R⁷ and R^(7′) are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄ haloalkylamino, or phenyl; and

R⁸ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆ alkylsulfonyl, C₁-C₆ trialkylsilyl, or phenyl;

-   -   or an agriculturally acceptable N-oxide or salt thereof.

In some embodiments:

X is N, CH, CF, CCl, or CBr;

R¹ is OR^(1′), wherein R^(1′) is hydrogen, C₁-C₈ alkyl, or C₇-C₁₀ arylalkyl;

R² is halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄-alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₄-alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, or C₁-C₄ haloalkylthio.

R³ and R⁴ are hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, or R³ and R⁴ taken together represent ═CR^(3′)(R^(4′)), wherein R^(3′) and R^(4′) are independently hydrogen, C₁-C₆ alkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl, C₁-C₆ alkoxy or C₁-C₆ alkylamino;

R⁶ and R^(6′) are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, CN, or NO₂;

R⁷ and R^(7′) are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, cyclopropyl, amino or C₁-C₄ alkylamino; and

R⁸ is hydrogen, C₁-C₆ alkyl, C₁-C₄ haloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, or C₁-C₆ alkylcarbamyl.

In some embodiments, X is N, CH or CF. In some embodiments, X is N. In some embodiments, X is CH. In some embodiments, X is CF. In other embodiments, X is C—CH₃.

In some embodiments, R² is halogen, C₂-C₄-alkenyl, C₂-C₄ haloalkenyl, or C₁-C₄-alkoxy.

In certain embodiments, R² is Cl, methoxy, vinyl, or 1-propenyl. In some embodiments, R³ and R⁴ are hydrogen.

In some embodiments, R⁶ is hydrogen or F. In certain embodiments, R⁶ is F. In certain embodiments, R⁶ is H. In some embodiments, R^(6′) is hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl, C₂-C₄ alkynyl, CN, or NO₂. In certain embodiments, R⁶ and R^(6′) are both hydrogen.

In certain embodiments, R⁷ and R^(7′) are both hydrogen.

In certain embodiments, R⁶, R^(6′), R⁷, and R^(7′) are all hydrogen.

In certain embodiments, X is CF, R¹ is OR^(1′), wherein R^(1′) is hydrogen, C₁-C₈ alkyl, or C₇-C₁₀ arylalkyl; R² is Cl, methoxy, vinyl, or 1-propenyl; R³ and R⁴ are hydrogen; R⁶ is hydrogen or F; and R^(6′) is hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl, C₂-C₄ alkynyl, CN, or NO₂.

In certain embodiments, the pyridine carboxylic acid herbicide can comprise a compound defined by Formula (IV):

wherein

X is N or CY, wherein Y is hydrogen, halogen, C₁-C₃ alkyl, C₁-C₃ haloalkyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio or C₁-C₃ haloalkylthio;

R¹ is OR^(1′) or NR^(1″)R^(1″′), wherein R^(1′) is hydrogen, C₁-C₈ alkyl, C₁-C₆ haloalkyl, or C₇-C₁₀ arylalkyl, and R^(1″) and R^(1″′) are independently hydrogen, C₁-C₁₂ alkyl, C₃-C₁₂ alkenyl, or C₃-C₁₂ alkynyl;

R² is hydrogen, F, Br, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄ haloalkylamino, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, cyano, or a group of the formula —CR¹⁷═CR¹⁸—SiR¹⁹R²⁰R²¹, wherein R¹⁷ is hydrogen, F, or Cl; R¹⁸ is hydrogen, F, Cl, C₁-C₄ alkyl, or C₁-C₄ haloalkyl; and R¹⁹, R²⁰, and R²¹ are independently C₁-C₁₀ alkyl, C₃-C₆ cycloalkyl, phenyl, substituted phenyl, C₁-C₁₀ alkoxy, or OH;

R³ and R⁴ are independently hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆ alkylsulfonyl, C₁-C₆ trialkylsilyl, C₁-C₆ dialkylphosphonyl, or R³ and R⁴ taken together with N is a 5- or 6-membered saturated ring, or R³ and R⁴ taken together represent ═CR^(3′)(R^(4′)), wherein R^(3′) and R^(4′) are independently hydrogen, C₁-C₆ alkyl, C₃-C₆ alkenyl, C₃-C₆ alkynyl, C₁-C₆ alkoxy or C₁-C₆ alkylamino, or, R^(3′) and R^(4′) taken together with ═C represent a 5- or 6-membered saturated ring;

A is A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15, A16, A17, A18, A19, A20, A21, A22, A23, A24, A25, A26, A27, A28, A29, A30, A31, A32, A33, A34, A35, or A36;

R⁵ is hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄ haloalkylamino, OH, or CN;

R⁶, R^(6′), and R⁶″ are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino or C₂-C₄ haloalkylamino, OH, CN, or NO₂;

R⁷ and R^(7′) are independently hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl, halocyclopropyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl, C₂-C₄ alkynyl, C₁-C₃ alkoxy, C₁-C₃ haloalkoxy, C₁-C₃ alkylthio, C₁-C₃ haloalkylthio, amino, C₁-C₄ alkylamino, C₂-C₄ haloalkylamino, or phenyl; and

R⁸ is hydrogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₃-C₆ alkenyl, C₃-C₆ haloalkenyl, C₃-C₆ alkynyl, formyl, C₁-C₃ alkylcarbonyl, C₁-C₃ haloalkylcarbonyl, C₁-C₆ alkoxycarbonyl, C₁-C₆ alkylcarbamyl, C₁-C₆ alkylsulfonyl, C₁-C₆ trialkylsilyl, or phenyl;

or an agriculturally acceptable N-oxide or salt thereof.

In some embodiments, X is N, CH or CF. In some embodiments, X is N. In some embodiments, X is CH. In some embodiments, X is CF. In other embodiments, X is C—CH₃.

In some embodiments, R² is C₂-C₄-alkenyl, C₂-C₄ haloalkenyl, or C₁-C₄-alkoxy. In certain embodiments, R² is methoxy, vinyl, 1-fluorovinyl, or 1-propenyl. In some embodiments, R³ and R⁴ are hydrogen.

In some embodiments, A is A1, A2, A3, A7, A8, A9, A10, A13, A14, or A15. In some embodiments, A is A1, A2, A3, A7, A8, A9, A10, A11, A13, A14, or A15. In some embodiments, A is A1, A2, A3, A7, A8, A9, A10, A13, A14, or A15. In certain embodiments, A is A2, A3, A8, A13, or A15. In certain embodiments, A is A1, A2, A3, A13, A14, or A15. In certain embodiments, A is A15.

In some embodiments, R⁵ is hydrogen or F. In certain embodiments, R⁵ is F. In certain embodiments, R⁵ is H.

In some embodiments, R⁶ is hydrogen or F. In certain embodiments, R⁶ is F. In certain embodiments, R⁶ is H. In some embodiments, R⁶″ is hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, cyclopropyl, C₂-C₄ alkynyl, CN, or NO₂. In certain embodiments, R⁶, R^(6′), and R⁶″ are all hydrogen.

In certain embodiments, the pyridine carboxylic acid herbicide can comprise one of Compounds 1-24, the structures of which are shown in the table below.

Compound No. Structure 1

2

3

4

5

6

7

8

9

10

11

12

13

14

15

16

17

18

19

20

21

22

23

24

In certain embodiments, the pyridine carboxylic acid herbicide can comprise 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl) picolinic acid, or an agriculturally acceptable N-oxide, salt, or ester thereof.

In some embodiments, the pyridine carboxylic acid herbicide can be provided as an agriculturally acceptable salt. Exemplary agriculturally acceptable salts of the pyridine carboxylic acid herbicides of Formula (I) include, but are not limited to, sodium salts, potassium salts, ammonium salts or substituted ammonium salts, in particular mono-, di- and tri-C₁-C₈-alkylammonium salts such as methyl ammonium, dimethylammonium and isopropylammonium, mono-, di- and tri-hydroxy-C₂-C₈-alkylammonium salts such as hydroxyethylammonium, di(hydroxyethyl)ammonium, tri(hydroxyethyl)ammonium, hydroxypropylammonium, di(hydroxypropyl)ammonium and tri(hydroxypropyl)ammonium salts, olamine salts, diglycolamine salts, choline salts, and quaternary ammonium salts such as those represented by the formula R⁹R¹⁰R¹¹R¹²N+ and wherein R⁹, R¹⁰, R¹¹ and R¹² (e.g., R⁹-R¹²) each independently can represent hydrogen, C₁-C₁₀ alkyl, C₂-C₈ alkenyl, C₂-C₈ alkynyl, C₁-C₈ alkoxy, C₁-C₈ alkylthio, or aryl groups, provided that R⁹-R¹² are sterically compatible.

In some embodiments, the pyridine carboxylic acid herbicide can be provided as an agriculturally acceptable ester. Suitable esters include, but are not limited to, C₁-C₈-alkyl esters and C₁-C₄-alkoxy-C₂-C₄-alkyl esters, such as methyl esters, ethyl esters, isopropyl, butyl, hexyl, heptyl, isoheptyl, isooctyl, 2-ethylhexyl, butoxyethyl esters, substituted or unsubstituted aryl esters, orthoesters, substituted or unsubstituted alkylaryl esters, and substituted or unsubstituted arylalkyl esters. In some embodiments, the ester can comprise a C₁-C₈ alkyl ester, wherein the C₁-C₈ alkyl group is optionally substituted with one or more moieties selected from the group consisting of cyano, C₂-C₈ alkoxy, and C₂-C₈ alkylsulfonyl. For example, the ester can comprise a methyl, —CH₂CN, —CH₂OCH₃, —CH₂OCH₂CH₂OCH₃, or —CH₂CH₂SO₂CH₃ ester.

The ester can also be an acetal (e.g., a cyclic acetal) formed by protection of the carbonyl group in the pyridine carboxylic acid herbicides described above (e.g., by Formula (I)). For example, the pyridine carboxylic acid herbicides described above can be reacted with a suitable diol (e.g., a diol such as ethane-1,2-diol or butane-2,3-diol, for example, using standard protecting group chemistry, such as taught in Greene, et al., Protective Groups in Organic Synthesis, John Wiley and Sons, Fourth Edition, 2007, hereby incorporated by reference) to form a cyclic acetal. In one embodiment, the ester can be a cyclic acetal defined by the structure below, where R², R³, R⁴, X, and A are as described above.

In some embodiments, the ester can comprise a substituted or unsubstituted benzyl ester. In some embodiments, the ester can comprise a benzyl ester optionally substituted with one or more moieties selected from the group consisting of halogen, C₁-C₂ alkyl, C₁-C₂ haloalkyl, and combinations thereof. In some embodiments, the ester can comprise a methyl ester.

The pyridine carboxylic acid herbicide, or an agriculturally acceptable N-oxide, salt, or ester thereof, can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect. In some embodiments, the pyridine carboxylic acid herbicide, or an agriculturally acceptable N-oxide, salt, or ester thereof, is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 0.1 grams of acid equivalent per hectare (g ae/ha) or greater (e.g., 0.2 g ae/ha or greater, 0.3 g ae/ha or greater, 0.4 g ae/ha or greater, 0.5 g ae/ha or greater, 0.6 g ae/ha or greater, 0.7 g ae/ha or greater, 0.8 g ae/ha or greater, 0.9 g ae/ha or greater, 1 g ae/ha or greater, 1.1 g ae/ha or greater, 1.2 g ae/ha or greater, 1.3 g ae/ha or greater, 1.4 g ae/ha or greater, 1.5 g ae/ha or greater, 1.6 g ae/ha or greater, 1.7 g ae/ha or greater, 1.8 g ae/ha or greater, 1.9 g ae/ha or greater, 2 g ae/ha or greater, 2.25 g ae/ha or greater, 2.5 g ae/ha or greater, 2.75 g ae/ha or greater, 3 g ae/ha or greater, 4 g ae/ha or greater, 5 g ae/ha or greater, 6 g ae/ha or greater, 7 g ae/ha or greater, 8 g ae/ha or greater, 9 g ae/ha or greater, 10 g ae/ha or greater, 11 g ae/ha or greater, 12 g ae/ha or greater, 13 g ae/ha or greater, 14 g ae/ha or greater, 15 g ae/ha or greater, 16 g ae/ha or greater, 17 g ae/ha or greater, 18 g ae/ha or greater, 19 g ae/ha or greater, 20 g ae/ha or greater, 21 g ae/ha or greater, 22 g ae/ha or greater, 23 g ae/ha or greater, 24 g ae/ha or greater, 25 g ae/ha or greater, 26 g ae/ha or greater, 27 g ae/ha or greater, 28 g ae/ha or greater, 29 g ae/ha or greater, 30 g ae/ha or greater, 31 g ae/ha or greater, 32 g ae/ha or greater, 33 g ae/ha or greater, 34 g ae/ha or greater, 35 g ae/ha or greater, 36 g ae/ha or greater, 37 g ae/ha or greater, 38 g ae/ha or greater, 39 g ae/ha or greater, 40 g ae/ha or greater, 41 g ae/ha or greater, 42 g ae/ha or greater, 43 g ae/ha or greater, 44 g ae/ha or greater, 45 g ae/ha or greater, 46 g ae/ha or greater, 47 g ae/ha or greater, 48 g ae/ha or greater, 49 g ae/ha or greater, 50 g ae/ha or greater, 55 g ae/ha or greater, 60 g ae/ha or greater, 65 g ae/ha or greater, 70 g ae/ha or greater, 75 g ae/ha or greater, 80 g ae/ha or greater, 85 g ae/ha or greater, 90 g ae/ha or greater, 95 g ae/ha or greater, 100 g ae/ha or greater, 110 g ae/ha or greater, 120 g ae/ha or greater, 130 g ae/ha or greater, 140 g ae/ha or greater, 150 g ae/ha or greater, 160 g ae/ha or greater, 170 g ae/ha or greater, 180 g ae/ha or greater, 190 g ae/ha or greater, 200 g ae/ha or greater, 210 g ae/ha or greater, 220 g ae/ha or greater, 230 g ae/ha or greater, 240 g ae/ha or greater, 250 g ae/ha or greater, 260 g ae/ha or greater, 270 g ae/ha or greater, 280 g ae/ha or greater, or 290 g ae/ha or greater).

In some embodiments, the pyridine carboxylic acid herbicide, or an agriculturally acceptable N-oxide, salt, or ester thereof, is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 300 g ae/ha or less (e.g., 290 g ae/ha or less, 280 g ae/ha or less, 270 g ae/ha or less, 260 g ae/ha or less, 250 g ae/ha or less, 240 g ae/ha or less, 230 g ae/ha or less, 220 g ae/ha or less, 210 g ae/ha or less, 200 g ae/ha or less, 190 g ae/ha or less, 180 g ae/ha or less, 170 g ae/ha or less, 160 g ae/ha or less, 150 g ae/ha or less, 140 g ae/ha or less, 130 g ae/ha or less, 120 g ae/ha or less, 110 g ae/ha or less, 100 g ae/ha or less, 95 g ae/ha or less, 90 g ae/ha or less, 85 g ae/ha or less, 80 g ae/ha or less, 75 g ae/ha or less, 70 g ae/ha or less, 65 g ae/ha or less, 60 g ae/ha or less, 55 g ae/ha or less, 50 g ae/ha or less, 49 g ae/ha or less, 48 g ae/ha or less, 47 g ae/ha or less, 46 g ae/ha or less, 45 g ae/ha or less, 44 g ae/ha or less, 43 g ae/ha or less, 42 g ae/ha or less, 41 g ae/ha or less, 40 g ae/ha or less, 39 g ae/ha or less, 38 g ae/ha or less, 37 g ae/ha or less, 36 g ae/ha or less, 35 g ae/ha or less, 34 g ae/ha or less, 33 g ae/ha or less, 32 g ae/ha or less, 31 g ae/ha or less, 30 g ae/ha or less, 29 g ae/ha or less, 28 g ae/ha or less, 27 g ae/ha or less, 26 g ae/ha or less, 25 g ae/ha or less, 24 g ae/ha or less, 23 g ae/ha or less, 22 g ae/ha or less, 21 g ae/ha or less, 20 g ae/ha or less, 19 g ae/ha or less, 18 g ae/ha or less, 17 g ae/ha or less, 16 g ae/ha or less, 15 g ae/ha or less, 14 g ae/ha or less, 13 g ae/ha or less, 12 g ae/ha or less, 11 g ae/ha or less, 10 g ae/ha or less, 9 g ae/ha or less, 8 g ae/ha or less, 7 g ae/ha or less, 6 g ae/ha or less, 5 g ae/ha or less, 4 g ae/ha or less, 3 g ae/ha or less, 2.75 g ae/ha or less, 2.5 g ae/ha or less, 2.25 g ae/ha or less, 2 g ae/ha or less, 1.9 g ae/ha or less, 1.8 g ae/ha or less, 1.7 g ae/ha or less, 1.6 g ae/ha or less, 1.5 g ae/ha or less, 1.4 g ae/ha or less, 1.3 g ae/ha or less, 1.2 g ae/ha or less, 1.1 g ae/ha or less, 1 g ae/ha or less, 0.9 g ae/ha or less, 0.8 g ae/ha or less, 0.7 g ae/ha or less, 0.6 g ae/ha or less, 0.5 g ae/ha or less, 0.4 g ae/ha or less, 0.3 g ae/ha or less, or 0.2 g ae/ha or less).

The pyridine carboxylic acid herbicide, or an agriculturally acceptable N-oxide, salt, or ester thereof, can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount ranging from any of the minimum values described above to any of the maximum values described above. In some embodiments, the pyridine carboxylic acid herbicide, or an agriculturally acceptable N-oxide, salt, or ester thereof, is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of from 0.1-300 g ae/ha (e.g., from 0.5-300 g ae/ha, from 0.5-5 g ae/ha, from 0.1-5 g ae/ha, from 2.5-40 g ae/ha, from 0.1-40 g ae/ha, from 0.5-40 g ae/ha, from 0.1-2.5 g ae/ha, from 0.5-2.5 g ae/ha, from 2-150 g ae/ha, from 5-75 g ae/ha, from 5-40 g ae/ha, from 30-40 g ae/ha, or from 5-15 g ae/ha). In some embodiments, the pyridine carboxylic acid herbicide, or an agriculturally acceptable N-oxide, salt, or ester thereof, is applied in an amount from 5-15 g ae/ha. In some embodiments, the pyridine carboxylic acid herbicide, or an agriculturally acceptable N-oxide, salt, or ester thereof, is applied in an amount from 5-40 g ae/ha.

Synthetic Auxin Herbicides

In addition to a pyridine carboxylic acid herbicide or agriculturally acceptable N-oxide, salt or ester thereof, the compositions can include a synthetic auxin herbicide. Synthetic auxin herbicides mimic natural plant hormones and can inhibit cell division and growth. Synthetic auxin herbicides include phenoxy herbicides, benzoic acid herbicides, and carboxylic acid herbicides.

In some embodiments, the composition can include a synthetic auxin herbicide selected from the group consisting of 4-CPA; 4-CPB; 4-CPP; 2,4-D; 2,4-DB; 3,4-DA; 3,4-DB; 3,4-DP; 2,4-DEP; 2,4-DEB; 2,4,5-T; 2,4,5-TB; 2,3,6-TBA, aminocyclopyrachlor, aminopyralid, clopyralid, dichlorprop, dichlorprop-P, dicamba, difenopenten, disul, diclofop, erbon, etnipromid, fenoprop, fluoxypyr, fluorxypyr-MHE, mecoprop, mecoprop-P, MCPA, MCPA-thioethyl, MCPB, naphthaleneacetamide, α-naphthaleneacetic acids, 1-naphthol, naphthoxyacetic acids, potassium naphthenate, picloram, quinclorac, quinmerac, sodium naphthenate, 4-aminopicolinic acid based herbicides, such as halauxifen, halauxifen-methyl, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoro-2-pyridinecarboxylic acid, benzyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoro-2-pyridinecarboxylate, and those described in U.S. Pat. Nos. 7,314,849 and 7,432,227 to Balko, et al., agriculturally acceptable salts and esters thereof, and combinations thereof. In some embodiments, the synthetic auxin herbicide can comprise 2,4-D, MCPA, dichlorprop, mecoprop, dicamba, clopyralid, fluroxypyr, halauxifen, agriculturally acceptable salts and esters thereof, or combinations thereof. In some embodiments, the synthetic auxin herbicide can comprise 2,4-DB, aminocyclopyrachlor, aminopyralid, picloram, quinclorac, triclopyr, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoro-2-pyridinecarboxylic acid, benzyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoro-2-pyridinecarboxylate, agriculturally acceptable salts and esters thereof, or combinations thereof.

2,4-D

In certain embodiments, the synthetic auxin herbicide can comprise 2,4-D or an agriculturally acceptable salt or ester thereof. 2,4-D, shown below, is a phenoxyacetic acid herbicide that provides broad spectrum control of many annual, biannual and perennial broad-leaved weeds and aquatic broad-leaved weeds in cereals, maize, sorghum, grasslands, established turf, grass seed crops, orchards (pome fruit and stone fruit), cranberries, asparagus, sugar cane, rice, forestry, and on non-crop land (including areas adjacent to water). 2,4-D, as well as methods of preparing 2,4-D, are known in the art. Its herbicidal activity is described, for example, in The Pesticide Manual, Sixteenth Edition, 2012.

In some embodiments, 2,4-D can be provided as an agriculturally acceptable salt or ester of 2,4-D. Exemplary agriculturally acceptable salts and esters of 2,4-D include, but are not limited to, 2,4-D-ammonium 2,4-D-butotyl, 2,4-D-2-butoxypropyl, 2,4-D-3-butoxypropyl, 2,4-D-butyl, 2,4-D choline, 2,4-D-diethylammonium, 2,4-D-dimethylammonium (2,4-D DMA), 2,4-D-diolamine, 2,4-D-dodecylammonium, 2,4-D-ethyl, 2,4-D-2-ethylhexyl (2,4-D EHE), 2,4-D-heptylammonium, 2,4-D-isobutyl, 2,4-D-isoctyl, 2,4-D-isopropyl, 2,4-D-isopropylammonium, 2,4-D-lithium, 2,4-D-meptyl, 2,4-D-methyl, 2,4-D-octyl, 2,4-D-pentyl, 2,4-D-propyl, 2,4-D-sodium, 2,4-D-tefuryl, 2,4-D-tetradecylammonium, 2,4-D-triethylammonium, 2,4-D-tris(2-hydroxypropyl)ammonium, 2,4-D-trolamine, and clacyfos. In some embodiments, the 2,4-D can be provided as 2,4-D-2-ethylhexyl (2,4-D EHE), shown below.

In some embodiments, 2,4-D can be provided as 2,4-D DMA, shown below.

In some embodiments, the 2,4-D can be provided as 2,4-D choline, shown below.

Exemplary uses of 2,4-D-choline include, but are not limited to, controlling annual and perennial broadleaf weeds, including, but not limited to, glyphosate-resistant broadleaf weeds. 2,4-D-Choline can be used in crops that have been made tolerant to 2,4-D, including, but not limited to, 2,4-D-tolerant soybeans, corn, and cotton. 2,4-D-Choline is generally, but is not required to be, applied post-emergent. 2,4-D-Choline can also be used for weed control in non-crop and perennial cropping systems.

MCPA

In certain embodiments, the synthetic auxin herbicide can comprise MCPA or an agriculturally acceptable salt or ester thereof. MCPA, shown below, is a phenoxyacetic acid herbicide that provides broad-spectrum control of many annual, biannual, and perennial broad-leaved weeds, woody weeds, and aquatic broad-leaved weeds in cereals, herbage seed crops, flax, rice, vines, peas, potatoes, asparagus, grassland, turf, under fruit trees, forestry, and on roadside verges and embankments. MCPA, as well as methods of preparing MCPA, are known in the art. Its herbicidal activity is described, for example, in The Pesticide Manual, Sixteenth Edition, 2012.

In some embodiments, MCPA can be provided as an agriculturally acceptable salt or ester of MCPA. Exemplary agriculturally acceptable salts of MCPA include, but are not limited to, MCPA-butotyl, MCPA-butyl, MCPA-dimethylammonium, MCPA-diolamine, MCPA-ethyl, MCPA-2-ethylhexyl (MCPA EHE), MCPA-isobutyl, MCPA-isoctyl, MCPA-isopropyl, MCPA-methyl, MCPA-olamine, MCPA-potassium, MCPA-sodium, MCPA-trolamine. In some embodiments, the MCPA can be provided as MCPA-2-ethylhexyl (MCPA EHE), shown below.

Dichlorprop

In certain embodiments, the synthetic auxin herbicide can comprise dichlorprop or an agriculturally acceptable salt or ester thereof. Dichlorprop, shown below, is a phenoxypropionic herbicide that provides broad-spectrum control of annual and perennial broad-leaved weeds in cereals and grasslands; brush control in non-crop land; control of broad-leaved aquatic weeds; and maintenance of embankments and roadside verges. Dichlorprop, as well as methods of making dichlorprop, are known in the art. Its herbicidal activity is described, for example, in The Pesticide Manual, Sixteenth Edition, 2012.

In some embodiments, dichlorprop can be provided as an agriculturally acceptable salt or ester of dichlorprop. Exemplary agriculturally acceptable salts and esters of dichlorprop include, but are not limited to, dichlorprop-butotyl, dichlorprop-dimethylammonium, dichlorprop-ethylammonium, dichlorprop-2-ethylhexyl, dichlorprop-isoctyl, dichlorprop-methyl, dichlorprop-potassium, dichlorprop-sodium, dichlorprop-P, dichlorprop-P-dimethylammonium, dichlorprop-P-2-ethylhexyl, dichlorprop-P-potassium, and dichlorprop-P-sodium. In some embodiments, the dichlorprop can be provided as dichlorprop-P, shown below.

Mecoprop

In certain embodiments, the synthetic auxin herbicide can comprise mecoprop or an agriculturally acceptable salt or ester thereof. Mecoprop, shown below, is a phenoxy carboxylic acid herbicide that provides broad-spectrum control of broad-leaved weeds in wheat, barley, oats, herbage seed crops, grassland, and under fruit trees and vines. Mecoprop also provides control of docks (Rumex spp.) in meadows and pastures. Mecoprop, as well as methods of making mecoprop, are known in the art. Its herbicidal activity is described in The Pesticide Manual, Sixteenth Edition, 2012.

In some embodiments, mecoprop can be provided as an agriculturally acceptable salt or ester of mecoprop. Exemplary agriculturally acceptable salts and esters of mecoprop include, but are not limited to, mecoprop-butotyl, mecoprop-potassium, mecoprop-sodium, mecoprop-dimethylammonium, mecoprop-diolamine, mecoprop-ethadyl, mecoprop-2-ethylhexyl, mecoprop-isoctyl, mecoprop-methyl, mecoprop-trolamine, mecoprop-P, mecoprop-P-butotyl, mecoprop-P-dimethylammonium, mecoprop-P-ethylhexyl, and mecoprop-P-potassium. In some embodiments, the mecoprop can be provided as mecoprop-P, shown below.

2,4-DB

In certain embodiments, the synthetic auxin herbicide can comprise 2,4-DB is a phenoxycarboxylic acid herbicide that provides post-emergence control of many annual and perennial broadleaf weeds in alfalfa, clovers, cereals and undersown cereals, grassland, forage legumes, soybeans, and peanuts. 2,4-DB, as well as methods of making 2,4-DB, are known in the art. Its herbicidal activity is described in The Pesticide Manual, Sixteenth Edition, 2012.

In some embodiments, 2,4-DB can be provided as an agriculturally acceptable salt or ester of 2,4-D. Exemplary agriculturally acceptable salts and esters of 2,4-DB include, but are not limited to, 2,4-DB-butyl, 2,4-DB-dimethylammonium (2,4-DB DMA), 2,4-DB-isoctyl, 2,4-DB-potassium, and 2,4-DB-sodium.

The synthetic auxin herbicide (e.g., 2,4-D, 2,4-DB, MCPA, dichlorprop, or mecoprop) or an agriculturally acceptable salt or ester thereof can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect. In some embodiments, the synthetic auxin herbicide or agriculturally acceptable salt or ester thereof is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 1 gram acid equivalent per hectare (g ae/ha) or greater (e.g., 2 g ae/ha or greater, 3 g ae/ha or greater, 4 g ae/ha or greater, 5 g ae/ha or greater, 10 g ae/ha or greater, 15 g ae/ha or greater, 20 g ae/ha or greater, 25 g ae/ha or greater, 30 g ae/ha or greater, 35 g ae/ha or greater, 40 g ae/ha or greater, 45 g ae/ha or greater, 50 g ae/ha or greater, 55 g ae/ha or greater, 60 g ae/ha or greater, 65 g ae/ha or greater, 70 g ae/ha or greater, 75 g ae/ha or greater, 80 g ae/ha or greater, 85 g ae/ha or greater, 90 g ae/ha or greater, 95 g ae/ha or greater, 100 g ae/ha or greater, 110 g ae/ha or greater, 120 g ae/ha or greater, 130 g ae/ha or greater, 140 g ae/ha or greater, 150 g ae/ha or greater, 160 g ae/ha or greater, 170 g ae/ha or greater, 180 g ae/ha or greater, 190 g ae/ha or greater, 200 g ae/ha or greater, 210 g ae/ha or greater, 220 g ae/ha or greater, 230 g ae/ha or greater, 240 g ae/ha or greater, 250 g ae/ha or greater, 260 g ae/ha or greater, 270 g ae/ha or greater, 280 g ae/ha or greater, 290 g ae/ha or greater, 300 g ae/ha or greater, 310 g ae/ha or greater, 320 g ae/ha or greater, 330 g ae/ha or greater, 340 g ae/ha or greater, 350 g ae/ha or greater, 360 g ae/ha or greater, 370 g ae/ha or greater, 380 g ae/ha or greater, 390 g ae/ha or greater, 400 g ae/ha or greater, 420 g ae/ha or greater, 440 g ae/ha or greater, 460 g ae/ha or greater, 480 g ae/ha or greater, 500 g ae/ha or greater, 520 g ae/ha or greater, 540 g ae/ha or greater, 560 g ae/ha or greater, 580 g ae/ha or greater, 600 g ae/ha or greater, 625 g ae/ha or greater, 650 g ae/ha or greater, 675 g ae/ha or greater, 700 g ae/ha or greater, 725 g ae/ha or greater, 750 g ae/ha or greater, 775 g ae/ha or greater, 800 g ae/ha or greater, 825 g ae/ha or greater, 850 g ae/ha or greater, 875 g ae/ha or greater, 900 g ae/ha or greater, 925 g ae/ha or greater, 950 g ae/ha or greater, 975 g ae/ha or greater, 1000 g ae/ha or greater, 1100 g ae/ha or greater, 1200 g ae/ha or greater, 1300 g ae/ha or greater, 1400 g ae/ha or greater, 1500 g ae/ha or greater, 1600 g ae/ha or greater, 1700 g ae/ha or greater, 1800 g ae/ha or greater, 1900 g ae/ha or greater, 2000 g ae/ha or greater, 2100 g ae/ha or greater, 2200 g ae/ha or greater, 2300 g ae/ha or greater, 2400 g ae/ha or greater, 2500 g ae/ha or greater, 2600 g ae/ha or greater, 2700 g ae/ha or greater, 2800 g ae/ha or greater, 2900 g ae/ha or greater, 3000 g ae/ha or greater, 3100 g ae/ha or greater, 3200 g ae/ha or greater, 3300 g ae/ha or greater, 3400 g ae/ha or greater, 3500 g ae/ha or greater, 3600 g ae/ha or greater, 3700 g ae/ha or greater, 3800 g ae/ha or greater, or 3900 g ae/ha or greater,).

In some embodiments, the synthetic auxin herbicide or agriculturally acceptable salt or ester thereof is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 4000 g ae/ha or less (e.g., 3900 g ae/ha or less, 3800 g ae/ha or less, 3700 g ae/ha or less, 3600 g ae/ha or less, 3500 g ae/ha or less, 3400 g ae/ha or less, 3300 g ae/ha or less, 3200 g ae/ha or less, 3100 g ae/ha or less, 3000 g ae/ha or less, 2900 g ae/ha or less, 2800 g ae/ha or less, 2700 g ae/ha or less, 2600 g ae/ha or less, 2500 g ae/ha or less, 2400 g ae/ha or less, 2300 g ae/ha or less, 2200 g ae/ha or less, 2100 g ae/ha or less, 2000 g ae/ha or less, 1900 g ae/ha or less, 1800 g ae/ha or less, 1700 g ae/ha or less, 1600 g ae/ha or less, 1500 g ae/ha or less, 1400 g ae/ha or less, 1300 g ae/ha or less, 1200 g ae/ha or less, 1100 g ae/ha or less, 1000 g ae/ha or less, 975 g ae/ha or less, 950 g ae/ha or less, 925 g ae/ha or less, 900 g ae/ha or less, 875 g ae/ha or less, 850 g ae/ha or less, 825 g ae/ha or less, 800 g ae/ha or less, 775 g ae/ha or less, 750 g ae/ha or less, 725 g ae/ha or less, 700 g ae/ha or less, 675 g ae/ha or less, 650 g ae/ha or less, 625 g ae/ha or less, 600 g ae/ha or less, 580 g ae/ha or less, 560 g ae/ha or less, 540 g ae/ha or less, 520 g ae/ha or less, 500 g ae/ha or less, 480 g ae/ha or less, 460 g ae/ha or less, 440 g ae/ha or less, 420 g ae/ha or less, 400 g ae/ha or less, 390 g ae/ha or less, 380 g ae/ha or less, 370 g ae/ha or less, 360 g ae/ha or less, 350 g ae/ha or less, 340 g ae/ha or less, 330 g ae/ha or less, 320 g ae/ha or less, 310 g ae/ha or less, 300 g ae/ha or less, 290 g ae/ha or less, 280 g ae/ha or less, 270 g ae/ha or less, 260 g ae/ha or less, 250 g ae/ha or less, 240 g ae/ha or less, 230 g ae/ha or less, 220 g ae/ha or less, 210 g ae/ha or less, 200 g ae/ha or less, 190 g ae/ha or less, 180 g ae/ha or less, 170 g ae/ha or less, 160 g ae/ha or less, 150 g ae/ha or less, 140 g ae/ha or less, 130 g ae/ha or less, 120 g ae/ha or less, 110 g ae/ha or less, 100 g ae/ha or less, 95 g ae/ha or less, 90 g ae/ha or less, 85 g ae/ha or less, 80 g ae/ha or less, 75 g ae/ha or less, 70 g ae/ha or less, 65 g ae/ha or less, 60 g ae/ha or less, 55 g ae/ha or less, 50 g ae/ha or less, 45 g ae/ha or less, 40 g ae/ha or less, 35 g ae/ha or less, 30 g ae/ha or less, 25 g ae/ha or less, 20 g ae/ha or less, 15 g ae/ha or less, 10 g ae/ha or less, 5 g ae/ha or less, 4 g ae/ha or less, 3 g ae/ha or less, or 2 g ae/ha or less).

The synthetic auxin herbicide or an agriculturally acceptable salt or ester thereof can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount ranging from any of the minimum values described above to any of the maximum values described above. In some embodiments, the synthetic auxin herbicide or agriculturally acceptable salt or ester thereof is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of from 1 g ae/ha to 4000 g ae/ha (e.g., 5 g ae/ha to 3000 g ae/ha, 1000-4000 g ae/ha, 1000-3000 g ae/ha, 1200-1500 g ae/ha, 280-2300 g ae/ha, 280-2250 g ae/ha, 1200-2700 g ae/ha, 450-800 g ae/ha, 100-400 g ae/ha, 70-300 g ae/ha, 10-400 g ae/ha, 50-400 g ae/ha, 5-1500 g ae/ha, 1500-3000 g ae/ha, 150-2500 g ae/ha, 2500-4000 g ae/ha, 1-900 g ae/ha, 900-1200 g ae/ha, 1-1000 g ae/ha, 1-850 g ae/ha, 1-800 g ae/ha, 1-760 g ae/ha, 1-700 g ae/ha, 1-660 g ae/ha, 1-620 g ae/ha, 1-600 g ae/ha, 1-560 g ae/ha, 5-750 g ae/ha, 750-1000 g ae/ha, 5-700 g ae/ha, 5-650 g ae/ha, 5-600 g ae/ha, 5-560 g ae/ha, 5-500 g ae/ha, 5-460 g ae/ha, 5-400 g ae/ha, 5-460 g ae/ha, 5-400 g ae/ha, 5-360 g ae/ha, 5-300 g ae/ha, 5-280 g ae/ha, 5-260 g ae/ha, 5-240 g ae/ha, 5-220 g ae/ha, 5-200 g ae/ha, 5-180 g ae/ha, 5-160 g ae/ha, 5-140 g ae/ha, 5-120 g ae/ha, 5-100 g ae/ha, 5-90 g ae/ha, 5-80 g ae/ha, 5-70 g ae/ha, 5-60 g ae/ha, 5-50 g ae/ha, 5-40 g ae/ha, 5-30 g ae/ha, 5-20 g ae/ha, 5-10 g ae/ha, 10-560 g ae/ha, 20-500 g ae/ha, 30-460 g ae/ha, 40-400 g ae/ha, 50-360 g ae/ha, 60-300 g ae/ha, 70-280 g ae/ha, 70-100 g ae/ha, 70-140 g ae/ha, 100-140 g ae/ha, 100-280 g ae/ha, 140-500 g ae/ha, 140-440 g ae/ha, 140-420 g ae/ha, 140-380 g ae/ha, 140-360 g ae/ha, 140-340 g ae/ha, 140-300 g ae/ha, 140-280 g ae/ha, 140-220 g ae/ha, 800-2000 g ae/ha, 600-1500 g ae/ha, 400-1000 g ae/ha, 1200-2000 g ae/ha, 1400-2500 g ae/ha, 2000-4000 g ae/ha, 1600-2400 g ae/ha, 40-350 g ae/ha, 40-200 g ae/ha, 1-210 g ae/ha, 1-240 g ae/ha, 1-180 g ae/ha, or 1-560 g ae/ha).

In certain embodiments, the herbicidal composition comprises a synergistic herbicidally effective amount of (a) a pyridine carboxylic acid herbicide or an agriculturally acceptable N-oxide, salt or ester thereof, and (b) 2,4-D, 2,4-DB, MCPA, dichlorprop, mecoprop, dicamba, clopyralid, fluroxypyr, halauxifen, picloram, triclopyr, aminocyclopyrachlor, aminopyralid, quinclorac, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoro-2-pyridinecarboxylic acid, or an agriculturally acceptable salt or ester thereof.

Dicamba

Compositions and methods of the present disclosure can include dicamba or an agriculturally acceptable salt or ester thereof. Dicamba, shown below, is a benzoic acid herbicide that provides broad-spectrum control of annual and perennial broad-leaved weeds and brush species in cereals, maize, sorghum, sugar cane, asparagus, perennial seed grasses, turf, pastures, range land, and non-crop land. Dicamba, as well as methods of making dicamba, are known in the art. Its herbicidal activity is described, for example, in The Pesticide Manual, Sixteenth Edition, 2012.

In some embodiments, dicamba can be provided as an agriculturally acceptable salt or ester of dicamba. Exemplary agriculturally acceptable salts and esters of dicamba include, but are not limited to, dicamba-diglycolamine, dicamba-dimethylammonium, dicamba-diolamine, dicamba-isopropylammonium, dicamba-methyl (disugran), dicamba-olamine, dicamba-potassium, dicamba-sodium, dicamba-trolamine, and cambendichlor.

Clopyralid

Compositions and methods of the present disclosure can include clopyralid or an agriculturally acceptable salt or ester thereof. Clopyralid, shown below, is a picolinic acid herbicide that provides broad-spectrum control of many annual and perennial broad-leaved weeds in sugar beet, fodder beet, spring rape, maize, cereals, brassicas, onions, leeks, strawberries flax, grassland and non-crop lands. Clopyralid, as well as methods of making clopyralid, are known in the art. Its herbicidal activity is described, for example, in The Pesticide Manual, Sixteenth Edition, 2012.

In some embodiments, clopyralid can be provided as an agriculturally acceptable salt or ester of clopyralid. Exemplary agriculturally acceptable salts and esters of clopyralid include, but are not limited to, clopyralid-methyl, clopyralid-olamine, clopyralid-potassium, and clopyralid-tris(2-hydroxypropyl)ammonium.

Fluroxypyr

Compositions and methods of the present disclosure can include fluroxypyr or an agriculturally acceptable salt or ester thereof. Fluroxypyr, shown below, is a pyridine carboxylic acid herbicide that provides protection against a variety of broad-leaved weeds in small grain crops, pastures, grasslands, orchards, plantation crops, maize, and forestry. Fluroxypyr, as well as methods of making fluroxypyr, are known in the art. Its herbicidal activity is described, for example, in The Pesticide Manual, Sixteenth Edition, 2012.

In some embodiments, fluroxypyr can be provided as an agriculturally acceptable salt or ester of fluroxypyr. Exemplary agriculturally acceptable salts and esters of fluroxypyr include, but are not limited to, fluroxypyr-butometyl and fluroxypyr-meptyl (fluroxypyr-MHE). In some embodiments, the fluroxypyr can be provided as fluroxypyr-meptyl (fluroxypyr-MHE), shown below.

Aminocyclopyrachlor

Compositions and methods of the present disclosure can include aminocyclo-pyrachlor or an agriculturally acceptable salt or ester thereof. Aminocyclopyrachlor is a pyrimidine carboxylic acid herbicide that provides control of broadleaf weeds and woody species, e.g., in rights-of-way, industrial sites, rangeland, permanent grass pastures and natural areas. Aminocyclopyrachlor, as well as methods of making amino-cyclopyrachlor, are known in the art. Its herbicidal activity is described in The Pesticide Manual, Sixteenth Edition, 2012.

In some embodiments, aminocyclopyrachlor can be provided as an agriculturally acceptable salt or ester of aminocyclopyrachlor. Exemplary agriculturally acceptable salts and esters of aminocyclopyrachlor include, but are not limited to, aminocyclopyrachlor-potassium and aminocyclopyrachlor-methyl.

Dicamba, clopyralid, fluroxypyr, aminocyclopyrachlor, or an agriculturally acceptable salts or esters thereof can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect. In some embodiments, the dicamba, clopyralid, fluroxypyr, aminocyclopyrachlor, or agriculturally acceptable salts or esters thereof can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 50 grams acid equivalent per hectare (g ae/ha) or greater (e.g., 60 g ae/ha or greater, 70 g ae/ha or greater, 80 g ae/ha or greater, 90 g ae/ha or greater, 100 g ae/ha or greater, 110 g ae/ha or greater, 120 g ae/ha or greater, 130 g ae/ha or greater, 140 g ae/ha or greater, 150 g ae/ha or greater, 160 g ae/ha or greater, 170 g ae/ha or greater, 180 g ae/ha or greater, 190 g ae/ha or greater, 200 g ae/ha or greater, 210 g ae/ha or greater, 220 g ae/ha or greater, 230 g ae/ha or greater, 240 g ae/ha or greater, 250 g ae/ha or greater, 260 g ae/ha or greater, 270 g ae/ha or greater, 280 g ae/ha or greater, 290 g ae/ha or greater, 300 g ae/ha or greater, 310 g ae/ha or greater, 320 g ae/ha or greater, 330 g ae/ha or greater, 340 g ae/ha or greater, 350 g ae/ha or greater, 360 g ae/ha or greater, 370 g ae/ha or greater, 380 g ae/ha or greater, or 390 g ae/ha or greater).

In some embodiments, the dicamba, clopyralid, fluroxypyr, aminocyclopyrachlor, or agriculturally acceptable salts or esters thereof can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 400 g ae/ha or less (e.g., 390 g ae/ha or less, 380 g ae/ha or less, 370 g ae/ha or less, 360 g ae/ha or less, 350 g ae/ha or less, 340 g ae/ha or less, 330 g ae/ha or less, 320 g ae/ha or less, 310 g ae/ha or less, 300 g ae/ha or less, 290 g ae/ha or less, 280 g ae/ha or less, 270 g ae/ha or less, 260 g ae/ha or less, 250 g ae/ha or less, 240 g ae/ha or less, 230 g ae/ha or less, 220 g ae/ha or less, 210 g ae/ha or less, 200 g ae/ha or less, 190 g ae/ha or less, 180 g ae/ha or less, 170 g ae/ha or less, 160 g ae/ha or less, 150 g ae/ha or less, 140 g ae/ha or less, 130 g ae/ha or less, 120 g ae/ha or less, 110 g ae/ha or less, 100 g ae/ha or less, 90 g ae/ha or less, 80 g ae/ha or less, 70 g ae/ha or less, or 60 g ae/ha or less).

The dicamba, clopyralid, fluroxypyr, aminocyclopyrachlor, or agriculturally acceptable salts or esters thereof can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount ranging from any of the minimum values described above to any of the maximum values described above. In some embodiments, the dicamba, clopyralid, fluroxypyr, aminocyclopyrachlor, or agriculturally acceptable salts or esters thereof can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of from 50 g ae/ha to 400 g ae/ha (e.g., 50-200 g ae/ha, 200-400 g ae/ha, 100-300 g ae/ha, 50-100 g ae/ha, 50-90 g ae/ha, or 60-80 g ae/ha).

Aminopyralid

Compositions and methods of the present disclosure can include aminopyralid or an agriculturally acceptable salt or ester thereof. Aminopyralid is a picolinic acid herbicide that provides long-term control of annual and perennial broadleaf weeds, e.g., in range and pasture. Aminocyclopyrachlor, as well as methods of making amino-cyclopyrachlor, are known in the art. Its herbicidal activity is described in The Pesticide Manual, Sixteenth Edition, 2012.

In some embodiments, aminopyralid can be provided as an agriculturally acceptable salt or ester of aminopyralid. Exemplary agriculturally acceptable salts and esters of aminopyralid include, but are not limited to, for example, aminopyralid-triisopropanolammonium (TIPA), shown below.

Halauxifen

In certain embodiments, the synthetic auxin inhibitor can comprise halauxifen or an agriculturally acceptable salt or ester thereof. Halauxifen, shown below, is an arylpicolinic acid herbicide that provides broad-spectrum control of broad-leaved weeds in cereal crops.

In some embodiments, halauxifen can be provided as an agriculturally acceptable salt or ester of halauxifen. Exemplary agriculturally acceptable salts and esters of halauxifen include, but are not limited to, halauxifen-methyl. In some embodiments, the halauxifen is provided as halauxifen-methyl, shown below.

4-Amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoro-2-pyridinecarboxylic acid

Compositions and methods of the present disclosure can include 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoro-2-pyridinecarboxylic acid or an agriculturally acceptable salt or ester thereof. 4-Amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoro-2-pyridinecarboxylic acid is arylpicolinic acid that has been described in U.S. Pat. No. 7,314,849 B2. Exemplary uses of 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoro-2-pyridinecarboxylic acid include controlling undesirable vegetation, including grass, broadleaf and sedge weeds, in multiple non-crop and cropping situations.

In some embodiments, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoro-2-pyridinecarboxylic acid can be provided as an agriculturally acceptable salt or ester of -amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoro-2-pyridinecarboxylic acid. Exemplary agriculturally acceptable salts and esters of 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoro-2-pyridinecarboxylic acid include, but are not limited to, benzyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylate, shown below.

The aminopyralid, halauxifen, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoro-2-pyridinecarboxylic acid, or agriculturally acceptable salts or esters thereof can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect. In some embodiments, aminopyralid, halauxifen, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoro-2-pyridinecarboxylic acid, or agriculturally acceptable salts or esters thereof is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 1 gram acid equivalent per hectare (g ae/ha) or greater (e.g., 1.5 g ae/ha or greater, 2 g ae/ha or greater, 2.5 g ae/ha or greater, 2 g ae/ha or greater, 2.5 g ae/ha or greater, 3 g ae/ha or greater, 4.5 g ae/ha or greater, 5 g ae/ha or greater, 5.5 g ae/ha or greater, 6 g ae/ha or greater, 6.5 g ae/ha or greater, 7 g ae/ha or greater, 7.5 g ae/ha or greater, 8 g ae/ha or greater, 8.5 g ae/ha or greater, 9 g ae/ha or greater, 9.5 g ae/ha or greater, 10 g ae/ha or greater, 12 g ae/ha or greater, 14 g ae/ha or greater, 16 g ae/ha or greater, 18 g ae/ha or greater, 20 g ae/ha or greater, 25 g ae/ha or greater, 30 g ae/ha or greater, 35 g ae/ha or greater, 40 g ae/ha or greater, 45 g ae/ha or greater, 50 g ae/ha or greater, 55 g ae/ha or greater, 60 g ae/ha or greater, 65 g ae/ha or greater, 70 g ae/ha or greater, 75 g ae/ha or greater, 80 g ae/ha or greater, 85 g ae/ha or greater, 90 g ae/ha or greater, 95 g ae/ha or greater, 100 g ae/ha or greater, 105 g ae/ha or greater, 110 g ae/ha or greater, 115 g ae/ha or greater, 120 g ae/ha or greater, 125 g ae/ha or greater, 130 g ae/ha or greater, 135 g ae/ha or greater, 140 g ae/ha or greater, or 145 g ae/ha or greater).

In some embodiments, aminopyralid, halauxifen, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoro-2-pyridinecarboxylic acid, or agriculturally acceptable salts or esters thereof is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 150 g ae/ha or less (e.g., 145 g ae/ha or less, 140 g ae/ha or less, 135 g ae/ha or less, 130 g ae/ha or less, 125 g ae/ha or less, 120 g ae/ha or less, 115 g ae/ha or less, 110 g ae/ha or less, 105 g ae/ha or less, 100 g ae/ha or less, 95 g ae/ha or less, 90 g ae/ha or less, 85 g ae/ha or less, 80 g ae/ha or less, 75 g ae/ha or less, 70 g ae/ha or less, 65 g ae/ha or less, 60 g ae/ha or less, 55 g ae/ha or less, 50 g ae/ha or less, 45 g ae/ha or less, 40 g ae/ha or less, 35 g ae/ha or less, 30 g ae/ha or less, 25 g ae/ha or less, 20 g ae/ha or less, 18 g ae/ha or less, 16 g ae/ha or less, 14 g ae/ha or less, 12 g ae/ha or less, 10 g ae/ha or less, 9.5 g ae/ha or less, 9 g ae/ha or less, 8.5 g ae/ha or less, 8 g ae/ha or less, 7.5 g ae/ha or less, 7 g ae/ha or less, 6.5 g ae/ha or less, 6 g ae/ha or less, 5.5 g ae/ha or less, 5 g ae/ha or less, 4.5 g ae/ha or less, 4 g ae/ha or less, 3.5 g ae/ha or less, 3 g ae/ha or less, 2.5 g ae/ha or less, 2 g ae/ha or less, or 1.5 g ae/ha or less).

The aminopyralid, halauxifen, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoro-2-pyridinecarboxylic acid, or agriculturally acceptable salts or esters thereof can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount ranging from any of the minimum values described above to any of the maximum values described above. In some embodiments, the aminopyralid, halauxifen, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoro-2-pyridinecarboxylic acid, or agriculturally acceptable salts or esters thereof is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of from 1 g ae/ha to 150 g ae/ha (e.g., 1-70 g ae/ha, 70-150 g ae/ha, 70-120 g ae/ha, 1-80 g ae/ha, 1-90 g ae/ha, or 20-80 g ae/ha).

Quinclorac

Compositions and methods of the present disclosure can include quinclorac or an agriculturally acceptable salt or ester thereof. Quinclorac, shown below, is a quinoline carboxylic acid herbicide that provides pre- and post-emergence control of grass weeds (Echinochloa spp., Aeschynomene spp., Sesbania spp.) and other weeds in direct-seeded and transplanted rice. Quinclorac, as well as methods of making quinclorac, are known in the art. Its herbicidal activity is described, for example, in The Pesticide Manual, Sixteenth Edition, 2012.

In some embodiments, quinclorac can be provided as an agriculturally acceptable salt or ester of quinclorac. Exemplary agriculturally acceptable salts and esters of quinclorac include, but are not limited to, quinclorac-dimethylammonium.

Picloram

In certain embodiments, the synthetic auxin herbicide can comprise picloram or an agriculturally acceptable salt or ester thereof. Picloram is a picolinic acid herbicide that provides management of unwanted vegetation, e.g., in rangeland, grass pastures, forestry, as well as non-crop land and right-of-way sites. Picloram, as well as methods of making picloram, are known in the art. Its herbicidal activity is described in The Pesticide Manual, Sixteenth Edition, 2012.

In some embodiments, picloram can be provided as an agriculturally acceptable salt or ester of picloram. Exemplary agriculturally acceptable salts and esters of picloram include, but are not limited to, picloram-dimethylammonium, picloram-isoctyl, picloram-potassium, picloram-triethylammonium, picloram-triisopropanolammonium (TIPA), picloram-triisopropylammonium, and picloram-trolamine (triethanolammonium). In some embodiments, the picloram can be provided as picloram-potassium, shown below.

In some embodiments, the picloram can be provided as picloram-TIPA, shown below.

Triclopyr

In certain embodiments, the synthetic auxin herbicide can include triclopyr or an agriculturally acceptable salt or ester thereof. Triclopyr is a picolinic acid herbicide that provides control of woody plants and broadleaf weed species, e.g., in grassland, uncultivated land, industrial areas, coniferous forests, rice and plantation crops. Triclopyr, as well as methods of making triclopyr, are known in the art. Its herbicidal activity is described in The Pesticide Manual, Sixteenth Edition, 2012.

In some embodiments, triclopyr can be provided as an agriculturally acceptable salt or ester of triclopyr. Exemplary agriculturally acceptable salts and esters of triclopyr include, but are not limited to, for example, triclopyr-triethylammonium (TEA), triclopyr choline, and triclopyr-butotyl (butoxyethyl or BEE). In some embodiments, the triclopyr can be provided as triclopyr-triethylammonium (TEA), shown below.

In some embodiments, the triclopyr can be provided as triclopyr-choline, shown below.

In some embodiments, the triclopyr can be provided as triclopyr-BEE, shown below.

The quinclorac, picloram, triclopyr, or agriculturally acceptable salts or esters thereof can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect. In some embodiments, the quinclorac, picloram, triclopyr, or agriculturally acceptable salts or esters thereof is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 10 grams acid equivalent per hectare (g ae/ha) or greater (e.g., 20 g ae/ha or greater, 30 g ae/ha or greater, 40 g ae/ha or greater, 50 g ae/ha or greater, 60 g ae/ha or greater, 70 g ae/ha or greater, 80 g ae/ha or greater, 90 g ae/ha or greater, 100 g ae/ha or greater, 200 g ae/ha or greater, 300 g ae/ha or greater, 400 g ae/ha or greater, 500 g ae/ha or greater, 600 g ae/ha or greater, 700 g ae/ha or greater, 800 g ae/ha or greater, 900 g ae/ha or greater, 1000 g ae/ha or greater, 1100 g ae/ha or greater, 1200 g ae/ha or greater, 1300 g ae/ha or greater, 1400 g ae/ha or greater, 1500 g ae/ha or greater, 1600 g ae/ha or greater, 1700 g ae/ha or greater, 1800 g ae/ha or greater, 1900 g ae/ha or greater, 2000 g ae/ha or greater, 2100 g ae/ha or greater, 2200 g ae/ha or greater, 2210 g ae/ha or greater, 2220 g ae/ha or greater, or 2230 g ae/ha or greater).

In some embodiments, the quinclorac, picloram, triclopyr, or agriculturally acceptable salts or esters thereof is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 2240 g ae/ha or less (e.g., 2230 g ae/ha or less, 2220 g ae/ha or less, 2210 g ae/ha or less, 2000 g ae/ha or less, 1900 g ae/ha or less, 1800 g ae/ha or less, 1700 g ae/ha or less, 1600 g ae/ha or less, 1500 g ae/ha or less, 1400 g ae/ha or less, 1300 g ae/ha or less, 1200 g ae/ha or less, 1100 g ae/ha or less, 1000 g ae/ha or less, 900 g ae/ha or less, 800 g ae/ha or less, 700 g ae/ha or less, 600 g ae/ha or less, 500 g ae/ha or less, 400 g ae/ha or less, 300 g ae/ha or less, 200 g ae/ha or less, 100 g ae/ha or less, 90 g ae/ha or less, 80 g ae/ha or less, 70 g ae/ha or less, 60 g ae/ha or less, 50 g ae/ha or less, 40 g ae/ha or less, or 30 g ae/ha or less).

The quinclorac, picloram, triclopyr, or agriculturally acceptable salts or esters thereof can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount ranging from any of the minimum values described above to any of the maximum values described above. In some embodiments, the quinclorac, picloram, triclopyr, or agriculturally acceptable salts or esters thereof is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of from 10 g ae/ha to 2240 g ae/ha (e.g., 1000-2240 g ae/ha, 10-1000 g ae/ha, 10-500 g ae/ha, 20-1200 g ae/ha, 50-1500 g ae/ha, 100-500 g ae/ha, or 150-750 g ae/ha).

Auxin Transport Inhibitors

In addition to the pyridine carboxylic acid herbicide or agriculturally acceptable N-oxide, salt or ester thereof, the compositions can include an auxin transport inhibitor. Auxin transport inhibitors inhibit polar transport of naturally occurring auxin, indoleacetic acid (IAA), and synthetic auxin-mimicking herbicides in sensitive plants. Examples of auxin transport inhibitors include phthalamate herbicides, semicarbazone herbicides, and others. In some embodiments, the auxin transport inhibitor can comprise a semicarbazone herbicide. In some embodiments, the auxin transport inhibitor can comprise a phthalamate herbicide. In some embodiments, the auxin transport inhibitor can comprise other benzoic acids.

In some embodiments, the composition can include an auxin transport inhibitor selected from the group consisting of diflufenzopyr, naptalam, 2,3,5-triiodobenzoic acid (2,3,5-TIBA), agriculturally acceptable salts and esters thereof, and combinations thereof.

Diflufenzopyr

In certain embodiments, the auxin transport inhibitor can comprise diflufenzopyr or an agriculturally acceptable salt or ester thereof. Diflufenzopyr, shown below, is a semicarbazone herbicide that provides control of broad-leaved and perennial weeds in maize, pastures, rangeland, and non-crop areas. Diflufenzopyr, as well as methods of preparing diflufenzopyr, are known in the art. Its herbicidal activity is described, for example, in The Pesticide Manual, Sixteenth Edition, 2012.

The auxin transport inhibitor (e.g., diflufenzopyr) or agriculturally acceptable salt or ester thereof can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect. In some embodiments, the auxin transport inhibitor (e.g., diflufenzopyr) or agriculturally acceptable salt or ester thereof is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 1 gram of acid equivalent per hectare (g ae/ha) or greater (e.g., 1.5 g ae/ha or greater, 2 g ae/ha or greater, 2.5 g ae/ha or greater, 3 g ae/ha or greater, 3.5 g ae/ha or greater, 4 g ae/ha or greater, 5 g ae/ha or greater, 6 g ae/ha or greater, 7 g ae/ha or greater, 8 g ae/ha or greater, 9 g ae/ha or greater, 10 g ae/ha or greater, 15 g ae/ha or greater, 20 g ae/ha or greater, 25 g ae/ha or greater, 30 g ae/ha or greater, 35 g ae/ha or greater, 40 g ae/ha or greater, 45 g ae/ha or greater, 50 g ae/ha or greater, 55 g ae/ha or greater, 60 g ae/ha or greater, 65 g ae/ha or greater, 70 g ae/ha or greater, 75 g ae/ha or greater, 80 g ae/ha or greater, 85 g ae/ha or greater, 90 g ae/ha or greater, 95 g ae/ha or greater, 100 g ae/ha or greater, 110 g ae/ha or greater, 120 g ae/ha or greater, 130 g ae/ha or greater, 140 g ae/ha or greater, 150 g ae/ha or greater, 160 g ae/ha or greater, 170 g ae/ha or greater, 180 g ae/ha or greater, 190 g ae/ha or greater, 200 g ae/ha or greater, 210 g ae/ha or greater, 220 g ae/ha or greater, 230 g ae/ha or greater, 240 g ae/ha or greater, 250 g ae/ha or greater, 260 g ae/ha or greater, 270 g ae/ha or greater, 280 g ae/ha or greater, 290 g ae/ha or greater, 300 g ae/ha or greater, 310 g ae/ha or greater, 320 g ae/ha or greater, 330 g ae/ha or greater, 340 g ae/ha or greater, 350 g ae/ha or greater, 360 g ae/ha or greater, 370 g ae/ha or greater, 380 g ae/ha or greater, 390 g ae/ha or greater, 400 g ae/ha or greater, 420 g ae/ha or greater, 440 g ae/ha or greater, 460 g ae/ha or greater, 480 g ae/ha or greater, 500 g ae/ha or greater, 520 g ae/ha or greater, 540 g ae/ha or greater, 560 g ae/ha or greater, 580 g ae/ha or greater, 600 g ae/ha or greater, 625 g ae/ha or greater, 650 g ae/ha or greater, 675 g ae/ha or greater, 700 g ae/ha or greater, 725 g ae/ha or greater, 750 g ae/ha or greater, 775 g ae/ha or greater, 800 g ae/ha or greater, 825 g ae/ha or greater, 850 g ae/ha or greater, 875 g ae/ha or greater, 900 g ae/ha or greater, 925 g ae/ha or greater, 950 g ae/ha or greater, or 975 g ae/ha or greater).

In some embodiments, the auxin transport inhibitor (e.g., diflufenzopyr) or agriculturally acceptable salt or ester thereof is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 1000 g ae/ha or less (e.g., 975 g ae/ha or less, 950 g ae/ha or less, 925 g ae/ha or less, 900 g ae/ha or less, 875 g ae/ha or less, 850 g ae/ha or less, 825 g ae/ha or less, 800 g ae/ha or less, 775 g ae/ha or less, 750 g ae/ha or less, 725 g ae/ha or less, 700 g ae/ha or less, 675 g ae/ha or less, 650 g ae/ha or less, 625 g ae/ha or less, 600 g ae/ha or less, 580 g ae/ha or less, 560 g ae/ha or less, 540 g ae/ha or less, 520 g ae/ha or less, 500 g ae/ha or less, 480 g ae/ha or less, 460 g ae/ha or less, 440 g ae/ha or less, 420 g ae/ha or less, 400 g ae/ha or less, 390 g ae/ha or less, 380 g ae/ha or less, 370 g ae/ha or less, 360 g ae/ha or less, 350 g ae/ha or less, 340 g ae/ha or less, 330 g ae/ha or less, 320 g ae/ha or less, 310 g ae/ha or less, 300 g ae/ha or less, 290 g ae/ha or less, 280 g ae/ha or less, 270 g ae/ha or less, 260 g ae/ha or less, 250 g ae/ha or less, 240 g ae/ha or less, 230 g ae/ha or less, 220 g ae/ha or less, 210 g ae/ha or less, 200 g ae/ha or less, 190 g ae/ha or less, 180 g ae/ha or less, 170 g ae/ha or less, 160 g ae/ha or less, 150 g ae/ha or less, 140 g ae/ha or less, 130 g ae/ha or less, 120 g ae/ha or less, 110 g ae/ha or less, 100 g ae/ha or less, 95 g ae/ha or less, 90 g ae/ha or less, 85 g ae/ha or less, 80 g ae/ha or less, 75 g ae/ha or less, 70 g ae/ha or less, 65 g ae/ha or less, 60 g ae/ha or less, 55 g ae/ha or less, 50 g ae/ha or less, 45 g ae/ha or less, 40 g ae/ha or less, 35 g ae/ha or less, 30 g ae/ha or less, 25 g ae/ha or less, 20 g ae/ha or less, 15 g ae/ha or less, 10 g ae/ha or less, 9 g ae/ha or less, 8 g ae/ha or less, 7 g ae/ha or less, 6 g ae/ha or less, 5 g ae/ha or less, 4 g ae/ha or less, 3.5 g ae/ha or less, 3 g ae/ha or less, 2.5 g ae/ha or less, 2 g ae/ha or less, or 1.5 g ae/ha or less).

The auxin transport inhibitor (e.g., diflufenzopyr) or an agriculturally acceptable salt or ester thereof can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount ranging from any of the minimum values described above to any of the maximum values described above. In some embodiments, the auxin transport inhibitor (e.g., diflufenzopyr) or agriculturally acceptable salt or ester thereof is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of from 1-1000 g ae/ha (e.g., from 1-750 g ae/ha, from 3.5-750 g ae/ha, from 3.5-700 g ae/ha, from 3.5-650 g ae/ha, from 3.5-600 g ae/ha, from 3.5-560 g ae/ha, from 3.5-500 g ae/ha, from 3.5-460 g ae/ha, from 3.5-400 g ae/ha, from 3.5-460 g ae/ha, from 3.5-400 g ae/ha, from 3.5-360 g ae/ha, from 3.5-300 g ae/ha, from 3.5-280 g ae/ha, from 3.5-260 g ae/ha, from 3.5-240 g ae/ha, from 3.5-220 g ae/ha, from 3.5-200 g ae/ha, from 3.5-180 g ae/ha, from 3.5-160 g ae/ha, from 3.5-140 g ae/ha, from 3.5-120 g ae/ha, from 3.5-100 g ae/ha, from 3.5-90 g ae/ha, from 3.5-80 g ae/ha, from 3.5-70 g ae/ha, from 3.5-60 g ae/ha, from 3.5-50 g ae/ha, from 3.5-40 g ae/ha, from 3.5-30 g ae/ha, from 3.5-20 g ae/ha, from 3.5-15 g ae/ha, from 3.5-10 g ae/ha, from 1-50 g ae/ha, from 1-40 g ae/ha, from 1-30 g ae/ha, from 1-20 g ae/ha, from 1-15 g ae/ha, from 1-10 g ae/ha, from 10-560 g ae/ha, from 20-500 g ae/ha, from 30-460 g ae/ha, from 40-400 g ae/ha, from 50-360 g ae/ha, from 60-300 g ae/ha, from 70-280 g ae/ha, from 70-100 g ae/ha, from 70-140 g ae/ha, from 100-140 g ae/ha, from 100-280 g ae/ha, or from 140-280 g ae/ha). In certain embodiments, the auxin transport inhibitor (e.g., diflufenzopyr) or agriculturally acceptable salt or ester thereof is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of from 3.5-15 g ae/ha.

Naptalam

In certain embodiments, the auxin transport inhibitor can comprise naptalam or an agriculturally acceptable salt or ester thereof. Naptalam is a phthalamate herbicide that provides pre-emergence control of many broad-leaved weeds and some grasses in cucurbits, asparagus, peanuts, soybeans, and established woody ornamentals. It is described in The Pesticide Manual, Fourteenth Edition, 2006. Exemplary forms of naptalam include its sodium salt.

2,3,5-Triiodobenzoic Acid

In certain embodiments, the auxin transport inhibitor can comprise 2,3,5-triiodobenzoic acid or an agriculturally acceptable salt or ester thereof. 2,3,5-Triiodobenzoic acid inhibits auxin efflux and thus blocks polar auxin movement between cells (Dhonukshe et al. Proc. Natl. Acad. Sci. 2008:105(11) 4489-4494).

The auxin transport inhibitor (e.g., naptalam or 2,3,5-triiodobenzoic acid) or agriculturally acceptable salts or esters thereof can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect. In some embodiments, the auxin transport inhibitor (e.g., naptalam or 2,3,5-triiodobenzoic acid) or agriculturally acceptable salts or esters thereof is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 140 grams acid equivalent per hectare (g ae/ha) or greater (e.g., 150 g ae/ha or greater, 200 g ae/ha or greater, 250 g ae/ha or greater, 300 g ae/ha or greater, 350 g ae/ha or greater, 400 g ae/ha or greater, 450 g ae/ha or greater, 500 g ae/ha or greater, 550 g ae/ha or greater, 600 g ae/ha or greater, 650 g ae/ha or greater, 700 g ae/ha or greater, 750 g ae/ha or greater, 800 g ae/ha or greater, 850 g ae/ha or greater, 900 g ae/ha or greater, 1000 g ae/ha or greater, 1100 g ae/ha or greater, 1200 g ae/ha or greater, 1300 g ae/ha or greater, 1400 g ae/ha or greater, 1500 g ae/ha or greater, 1600 g ae/ha or greater, 1700 g ae/ha or greater, 1800 g ae/ha or greater, 1900 g ae/ha or greater, 2000 g ae/ha or greater, 2200 g ae/ha or greater, 2400 g ae/ha or greater, 2600 g ae/ha or greater, 2800 g ae/ha or greater, 3000 g ae/ha or greater, 3200 g ae/ha or greater, 3400 g ae/ha or greater, 3600 g ae/ha or greater, 3800 g ae/ha or greater, 3850 g ae/ha or greater, 3900 g ae/ha or greater, 3950 g ae/ha or greater, 4000 g ae/ha or greater, 4050 g ae/ha or greater, 4100 g ae/ha or greater, 4150 g ae/ha or greater, 4200 g ae/ha or greater, 4250 g ae/ha or greater, 4300 g ae/ha or greater, 4350 g ae/ha or greater, 4400 g ae/ha or greater, 4450 g ae/ha or greater, 4500 g ae/ha or greater, 4550 g ae/ha or greater, 4600 g ae/ha or greater, 4650 g ae/ha or greater, 4700 g ae/ha or greater, 4750 g ae/ha or greater, 4800 g ae/ha or greater, 4850 g ae/ha or greater, 4900 g ae/ha or greater, 4950 g ae/ha or greater, 5000 g ae/ha or greater, 5050 g ae/ha or greater, 5100 g ae/ha or greater, 5150 g ae/ha or greater, 5200 g ae/ha or greater, 5250 g ae/ha or greater, 5300 g ae/ha or greater, 5350 g ae/ha or greater, 5400 g ae/ha or greater, or 5450 g ae/ha or greater).

In some embodiments, the auxin transport inhibitor (e.g., naptalam or 2,3,5-triiodobenzoic acid) or agriculturally acceptable salt or ester thereof is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 5500 g ae/ha or less (e.g., 5450 g ae/ha or less, 5400 g ae/ha or less, 5350 g ae/ha or less, 5300 g ae/ha or less, 5250 g ae/ha or less, 5200 g ae/ha or less, 5150 g ae/ha or less, 5100 g ae/ha or less, 5050 g ae/ha or less, 5000 g ae/ha or less, 4950 g ae/ha or less, 4900 g ae/ha or less, 4850 g ae/ha or less, 4800 g ae/ha or less, 4750 g ae/ha or less, 4700 g ae/ha or less, 4650 g ae/ha or less, 4600 g ae/ha or less, 4550 g ae/ha or less, 4500 g ae/ha or less, 4450 g ae/ha or less, 4400 g ae/ha or less, 4350 g ae/ha or less, 4300 g ae/ha or less, 4250 g ae/ha or less, 4200 g ae/ha or less, 4150 g ae/ha or less, 4100 g ae/ha or less, 4050 g ae/ha or less, 4000 g ae/ha or less, 3950 g ae/ha or less, 3900 g ae/ha or less, 3850 g ae/ha or less, 3800 g ae/ha or less, 3600 g ae/ha or less, 3400 g ae/ha or less, 3200 g ae/ha or less, 3000 g ae/ha or less, 2800 g ae/ha or less, 2600 g ae/ha or less, 2400 g ae/ha or less, 2200 g ae/ha or less, 2000 g ae/ha or less, 1900 g ae/ha or less, 1800 g ae/ha or less, 1700 g ae/ha or less, 1600 g ae/ha or less, 1500 g ae/ha or less, 1400 g ae/ha or less, 1300 g ae/ha or less, 1200 g ae/ha or less, 1100 g ae/ha or less, 1000 g ae/ha or less, 900 g ae/ha or less, 800 g ae/ha or less, 750 g ae/ha or less, 700 g ae/ha or less, 650 g ae/ha or less, 600 g ae/ha or less, 550 g ae/ha or less, 500 g ae/ha or less, 450 g ae/ha or less, 400 g ae/ha or less, 350 g ae/ha or less, 300 g ae/ha or less, 250 g ae/ha or less, 200 g ae/ha or less, or 150 g ae/ha or less).

The auxin transport inhibitor (e.g., naptalam or 2,3,5-triiodobenzoic acid) or an agriculturally acceptable salt or ester thereof can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount ranging from any of the minimum values described above to any of the maximum values described above. In some embodiments, the auxin transport inhibitor (e.g., naptalam or 2,3,5-triiodobenzoic acid) or agriculturally acceptable salt or ester thereof is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of from 140-5500 g ae/ha (e.g., 140-3000 g ae/ha, 3000-5500 g ae/ha, 140-2000 g ae/ha, 1400-3500 g ae/ha, 200-2000 g ae/ha, 200-3000 g ae/ha, 200-4000 g ae/ha, 250-2000 g ae/ha, 250-3000 g ae/ha, 250-4000 g ae/ha, 300-2000 g ae/ha, 300-3000 g ae/ha, 300-4000 g ae/ha, 500-2000 g ae/ha, 500-3000 g ae/ha, 500-4000 g ae/ha, or 1000-3000 g ae/ha). In certain embodiments, the auxin transport inhibitor (e.g., naptalam or 2,3,5-triiodobenzoic acid) or agriculturally acceptable salt or ester thereof is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of from 2000-3000 g ae/ha.

II. Compositions

A. Herbicidal Mixtures or Combinations

The (a) a pyridine carboxylic acid herbicide or an agriculturally acceptable N-oxide, salt, or ester thereof is mixed with or applied in combination with (b) a synthetic auxin herbicide, auxin transport inhibitor, agriculturally acceptable salts or esters thereof, or combinations thereof. In some embodiments, (a) and (b) can be provided in an amount sufficient to induce a herbicidal effect. In some embodiments, (a) and (b) are used in an amount sufficient to induce a synergistic herbicidal effect while still showing good crop compatibility (i.e., their use in crops does not result in increased damage to crops when compared to the individual application of the herbicidal compounds (a) or (b)). As described in the Herbicide Handbook of the Weed Science Society of America, Tenth Edition, 2014, p. 487, “‘synergism’ [is] an interaction of two or more factors such that the effect when combined is greater than the predicted effect based on the response to each factor applied separately.” Synergistic in the herbicide context can mean that the use of (a) and (b) as defined above results in an increased weed control effect compared to the weed control effects that are possible with the use of (a) or (b) alone. In some embodiments, the damage or injury to the undesired vegetation caused by the compositions and methods disclosed herein is evaluated using a scale from 0% to 100%, when compared with the untreated control vegetation, wherein 0% indicates no damage to the undesired vegetation and 100% indicates complete destruction of the undesired vegetation. In some embodiments, Colby's formula is applied to determine whether using (a) and (b) in combination shows a synergistic effect: S. R. Colby, Calculating Synergistic and Antagonistic Responses of Herbicide Combinations, WEEDS 15, p. 22 (1967)

$E = {X + Y - \frac{X \star Y}{100}}$

wherein

X=effect in percent using (a) a pyridine carboxylic acid herbicide or an agriculturally acceptable N-oxide, salt, or ester thereof at an application rate a;

Y=effect in percent using (b) a synthetic auxin herbicide, auxin transport inhibitor, agriculturally acceptable salts or esters thereof, or combinations thereof at an application rate b;

E=expected effect (in %) of (a)+(b) at application rates a and b.

In Colby's equation, the value E corresponds to the effect (plant damage or injury) that is to be expected if the activity of the individual compounds is additive. If the observed effect is higher than the value E calculated according to the Colby equation, then a synergistic effect is present according to the Colby equation.

In some embodiments, the compositions and methods disclosed herein are synergistic as defined by the Colby equation. In some embodiments, the joint action of (a) a pyridine carboxylic acid herbicide or an agriculturally acceptable N-oxide, salt, or ester thereof and (b) a synthetic auxin herbicide, auxin transport inhibitor, agriculturally acceptable salts or esters thereof, or combinations thereof results in enhanced activity against undesired vegetation (via synergism), even at application rates below those typically used for the pesticide to have a herbicidal effect on its own. In some embodiments, the compositions and methods disclosed herein can, based on the individual components, be used at lower application rates to achieve a herbicidal effect comparable to the effect produced by the individual components at normal application rates. In some embodiments, the compositions and methods disclosed herein provide an accelerated action on undesired vegetation (i.e., they effect damaging of undesired vegetation more quickly compared with application of the individual herbicides).

In some embodiments, the observed effect for undesired vegetation is at least 1%, at least 2%, at least 3%, at least 4%, at least 5%, at least 10%, at least 15%, at least 20%, or at least 25% greater than the effect (E) calculated according to the Colby equation (e.g., an observed effect of 96% would be 4% greater than an calculated effect (E) of 92%). In some embodiments, for undesired vegetation, the difference (Do) between 100% and the observed effect is at least 5%, at least 10%, at least 15%, at least 20%, at least 25%, at least 30%, at least 35%, at least 40%, at least 45%, or at least 50% less than the difference (DE) between 100% and the effect (E) calculated according to the Colby equation (e.g., an observed effect of 96% would produce a Do of 4%, a calculated effect (E) of 92% would produce a DE of 8%, and Do would be 50% less than or half of DE).

In some embodiments, the weight ratio of (a) a pyridine carboxylic acid herbicide or an agriculturally acceptable N-oxide, salt, or ester thereof to (b) a synthetic auxin herbicide, or an agriculturally acceptable salt or ester thereof is 1:8000 or more (e.g., 1:7800 or more, 1:7600 or more, 1:7400 or more, 1:7200 or more, 1:7000 or more, 1:6750 or more, 1:6500 or more, 1:6250 or more, 1:6000 or more, 1:5750 or more, 1:5500 or more, 1:5250 or more, 1:5000 or more, 1:4500 or more, 1:4000 or more, 1:3500 or more, 1:3000 or more 1:2900 or more, 1:2800 or more, 1:2700 or more, 1:2600 or more, 1:2500 or more, 1:2400 or more, 1:2300 or more, 1:2200 or more, 1:2100 or more, 1:2000 or more, 1:1900 or more, 1:1800 or more, 1:1750 or more 1:1700 or more, 1:1600 or more, 1:1500 or more, 1:1400 or more, 1:1300 or more, 1:1250 or more, 1:1200 or more, 1:1100 or more, 1:1000 or more, 1:900 or more, 1:800 or more, 1:700 or more, 1:600 or more, 1:500 or more, 1:400 or more, 1:300 or more, 1:200 or more, 1:100 or more, 1:90 or more, 1:80 or more, 1:70 or more, 1:60 or more, 1:50 or more, 1:45 or more, 1:40 or more, 1:35 or more, 1:30 or more, 1:25 or more, 1:20 or more, 1:15 or more, 1:10 or more, 1:9 or more, 1:8 or more, 1:7 or more, 1:6 or more, 1:5 or more, 1:4.75 or more, 1:4.5 or more, 1:4.25 or more, 1:4 or more, 1:3.75 or more, 1:3.5 or more, 1:3.25 or more, 1:3 or more, 1:2.75 or more, 1:2.5 or more, 1:2.25 or more, 1:2 or more, 1:1.9 or more, 1:1.8 or more, 1:1.7 or more, 1:1.6 or more, 1:1.5 or more, 1:1.4 or more, 1:1.3 or more, 1:1.2 or more, 1:1.1 or more, 1:1 or more, 1.1:1 or more, 1.2:1 or more, 1.3:1 or more, 1.4:1 or more, 1.5:1 or more, 1.6:1 or more, 1.7:1 or more, 1.8:1 or more, 1.9:1 or more, 2:1 or more, 2.25:1 or more, 2.5:1 or more, 2.75:1 or more, 3:1 or more, 3.25:1 or more, 3.5:1 or more, 3.75:1 or more, 4:1 or more, 4.25:1 or more, 4.5:1 or more, 4.75:1 or more, 5:1 or more, 6:1 or more, 7:1 or more, 8:1 or more, 9:1 or more, 10:1 or more, 15:1 or more, 20:1 or more, 25:1 or more, 30:1 or more, 35:1 or more, 40:1 or more, 45:1 or more, 50:1 or more, 55:1 or more, 60:1 or more, 70:1 or more, 80:1 or more, 90:1 or more, 100:1 or more, 120:1 or more, 140:1 or more, 160:1 or more, 180:1 or more, 200:1 or more, 220:1 or more, 240:1 or more, 260:1 or more, or 280:1 or more).

In some embodiments, the weight ratio of (a) a pyridine carboxylic acid herbicide or an agriculturally acceptable N-oxide, salt, or ester thereof to (b) a synthetic auxin herbicide, or an agriculturally acceptable salt or ester thereof is 300:1 or less (e.g., 280:1 or less, 260:1 or less, 240:1 or less, 220:1 or less, 200:1 or less, 180:1 or less, 160:1 or less, 140:1 or less, 120:1 or less, 100:1 or less, 90:1 or less, 80:1 or less, 70:1 or less, 60:1 or less, 55:1 or less, 50:1 or less, 45:1 or less, 40:1 or less, 35:1 or less, 30:1 or less, 25:1 or less, 20:1 or less, 15:1 or less, 10:1 or less, 9:1 or less, 8:1 or less, 7:1 or less, 6:1 or less, 5:1 or less, 4.75:1 or less, 4.5:1 or less, 4.25:1 or less, 4:1 or less, 3.75:1 or less, 3.5:1 or less, 3.25:1 or less, 3:1 or less, 2.75:1 or less, 2.5:1 or less, 2.25:1 or less, 2:1 or less, 1.9:1 or less, 1.8:1 or less, 1.7:1 or less, 1.6:1 or less, 1.5:1 or less, 1.4:1 or less, 1.3:1 or less, 1.2:1 or less, 1.1:1 or less, 1:1 or less, 1:1.1 or less, 1:1.2 or less, 1:1.3 or less, 1:1.4 or less, 1:1.5 or less, 1:1.6 or less, 1:1.7 or less, 1:1.8 or less, 1:1.9 or less, 1:2 or less, 1:2.25 or less, 1:2.5 or less, 1:2.75 or less, 1:3 or less, 1:3.25 or less, 1:3.5 or less, 1:3.75 or less, 1:4 or less, 1:4.25 or less, 1:4.5 or less, 1:4.75 or less, 1:5 or less, 1:6 or less, 1:7 or less, 1:8 or less, 1:9 or less, 1:10 or less, 1:15 or less, 1:20 or less, 1:25 or less, 1:30 or less, 1:35 or less, 1:40 or less, 1:45 or less, 1:50 or less, 1:60 or less, 1:70 or less, 1:80 or less, 1:90 or less, 1:100 or less, 1:200 or less, 1:300 or less, 1:400 or less, 1:500 or less, 1:600 or less, 1:700 or less, 1:800 or less, 1:900 or less, 1:1000 or less, 1:1100 or less, 1:1200 or less, 1:1250 or less, 1:1300 or less, 1:1400 or less, 1:1500 or less, 1:1600 or less, 1:1700 or less, 1:1750 or less, 1:1800 or less, 1:1900 or less, 1:2000 or less, 1:2100 or less, 1:2200 or less, 1:2300 or less, 1:2400 or less, 1:2500 or less, 1:2600 or less, 1:2700 or less, 1:2800 or less, 1:2900 or less, 1:3000 or less, 1:3500 or less, 1:4000 or less, 1:4500 or less, 1:5000 or less, 1:5250 or less, 1:5500 or less, 1:5750 or less, 1:6000 or less, 1:6250 or less, 1:6500 or less, 1:6750 or less, 1:7000 or less, 1:7200 or less, 1:7400 or less, 1:7600 or less, or 1:7800 or less).

The weight ratio of (a) a pyridine carboxylic acid herbicide or an agriculturally acceptable N-oxide, salt, or ester thereof to (b) a synthetic auxin herbicide, or an agriculturally acceptable salt or ester thereof can range from any of the minimum ratios described above to any of the maximum values described above. In some embodiments, the weight ratio of (a) a pyridine carboxylic acid herbicide or an agriculturally acceptable N-oxide, salt, or ester thereof to (b) a synthetic auxin herbicide, or an agriculturally acceptable salt or ester thereof is from 1:8000 to 300:1 (e.g., from 1:7000 to 260:1, from 1:6000 to 220:1, from 1:5000 to 200:1, from 1:4000 to 160:1, from 1:3000 to 120:1, from 1:2000 to 100:1, from 1:1000 to 80:1, from 1:750 to 75:1, from 1:500 to 50:1, from 1:350 to 40:1, from 1:225 to 30:1, from 1:200 to 25:1, from 1:200 to 20:1, from 1:180 to 15:1, from 1:160 to 12:1, from 1:150 to 10:1, from 1:100 to 8:1, from 1:90 to 5:1, from 1:80 to 3.5:1, from 1:70 to 7:1, 1:3000 to 60:1, from 1:2500 to 50:1, from 1:2000 to 40:1, from 1:1500 to 30:1, from 1:1000 to 20:1, from 1:900 to 10:1, from 1:800 to 9:1, from 1:700 to 8:1, from 1:600 to 8:1, from 1:500 to 8:1, from 1:400 to 8:1, from 1:300 to 8:1, from 1:900 to 50:1, from 1:800 to 40:1, from 1:700 to 30:1, from 1:600 to 20:1, from 1:500 to 15:1, from 1:400 to 10:1, from 1:300 to 9:1, from 1:200 to 8:1, from 1:100 to 7:1, from 1:50 to 6:1, from 1:40 to 5:1, from 1:30 to 4:1, from 1:20 to 3:1, from 1:10 to 2:1, from 1:5 to 5:1, from 1:4 to 4:1, from 1:3 to 3:1, from 1:2 to 2:1 from 1:1.9 to 1.9:1, from 1:1.8 to 1.8:1, from 1:1.7 to 1.7:1, from 1:1.6 to 1.6:1, from 1:1.5 to 1.5:1, from 1:1.4 to 1.4:1, from 1:1.5 to 1.3:1, from 1:1.2 to 1.2:1, from 1:1.1 to 1.1:1, from 1:35 to 1:1, from 1:34 to 1:1, from 1:33 to 1:1, from 1:32 to 1:1, from 1:31 to 1:1, from 1:30 to 1:1, from 1:29 to 1:1, from 1:28 to 1:1, from 1:27 to 1:1, from 1:26 to 1:1, from 1:25 to 1:1, from 1:24 to 1:1, from 1:23 to 1:1, from 1:22 to 1:1, from 1:21 to 1:1, from 1:20 to 1:1, from 1:19 to 1:1, from 1:18 to 1:1, from 1:17 to 1:1, from 1:16 to 1:1, from 1:15 to 1:1, from 1:14 to 1:1, from 1:13 to 1:1, from 1:12 to 1:1, from 1:11 to 1:1, from 1:10 to 1:1, from 1:9 to 1:1, from 1:8 to 1:1, from 1:7 to 1:1, from 1:6 to 1:1, from 1:5 to 1:1, from 1:4 to 1:1, from 1:3 to 1:1, from 1:2 to 1:1, from 1:1.9 to 1:1, from 1:1.8 to 1:1, from 1:1.7 to 1:1, from 1:1.6 to 1:1, from 1:1.5 to 1:1, from 1:1.4 to 1:1, from 1:1.3 to 1:1, from 1:1.2 to 1:1, or from 1:1.1 to 1:1).

In some embodiments, (b) includes dicamba, clopyralid, fluroxypyr, aminocyclopyrachlor, or an agriculturally acceptable salt or ester thereof. In some embodiments, the weight ratio of (a) a pyridine carboxylic acid herbicide or an agriculturally acceptable N-oxide, salt, or ester thereof to (b) dicamba or an agriculturally acceptable salt or ester thereof is 1:800 or more (e.g., 1:700 or more, 1:600 or more, 1:500 or more, 1:400 or more, 1:300 or more, 1:200 or more, 1:100 or more, 1:90 or more, 1:80 or more, 1:70 or more, 1:60 or more, 1:50 or more, 1:45 or more, 1:40 or more, 1:35 or more, 1:30 or more, 1:25 or more, 1:20 or more, 1:15 or more, 1:10 or more, 1:9 or more, 1:8 or more, 1:7 or more, 1:6 or more, 1:5 or more, 1:4.75 or more, 1:4.5 or more, 1:4.25 or more, 1:4 or more, 1:3.75 or more, 1:3.5 or more, 1:3.25 or more, 1:3 or more, 1:2.75 or more, 1:2.5 or more, 1:2.25 or more, 1:2 or more, 1:1.9 or more, 1:1.8 or more, 1:1.7 or more, 1:1.6 or more, 1:1.5 or more, 1:1.4 or more, 1:1.3 or more, 1:1.2 or more, 1:1.1 or more, 1:1 or more, 1.1:1 or more, 1.2:1 or more, 1.3:1 or more, 1.4:1 or more, 1.5:1 or more, 1.6:1 or more, 1.7:1 or more, 1.8:1 or more, 1.9:1 or more, 2:1 or more, 2.1:1 or more, 2.2:1 or more, 2.3:1 or more, 2.4:1 or more, 2.5:1 or more, 2.6:1 or more, 2.7:1 or more, 2.8:1 or more, 2.9:1 or more, 3:1 or more, 3.2:1 or more, 3.4:1 or more, 3.6:1 or more, 3.8:1 or more, 4:1 or more, 4.2:1 or more, 4.4:1 or more, 4.6:1 or more, 4.8:1 or more, 5:1 or more, 5.1:1 or more, 5.2:1 or more, 5.3:1 or more, 5.4:1 or more, 5.5:1 or more, 5.6:1 or more, 5.7:1 or more, 0.5.8:1 or more, or 5.9:1 or more).

In some embodiments, the weight ratio of (a) a pyridine carboxylic acid herbicide or an agriculturally acceptable N-oxide, salt, or ester thereof to (b) dicamba, clopyralid, fluroxypyr, aminocyclopyrachlor, or an agriculturally acceptable salt or ester thereof is 6:1 or less (e.g., 5.9:1 or less, 5.8:1 or less, 5.7:1 or less, 5.6:1 or less, 5.5:1 or less, 5.4:1 or less, 5.3:1 or less, 5.2:1 or less, 5.1:1 or less, 5:1 or less, 4.8:1 or less, 4.6:1 or less, 4.4:1 or less, 4.2:1 or less, 4:1 or less, 3.8:1 or less, 3.6:1 or less, 3.4:1 or less, 3.2:1 or less, 3:1 or less, 2.9:1 or less, 2.8:1 or less, 2.7:1 or less, 2.6:1 or less, 2.5:1 or less, 2.4:1 or less, 2.3:1 or less, 2.2:1 or less, 2.1:1 or less, 2:1 or less, 1.9:1 or less, 1.8:1 or less, 1.7:1 or less, 1.6:1 or less, 1.5:1 or less, 1.4:1 or less, 1.3:1 or less, 1.2:1 or less, 1.1:1 or less, 1:1 or less, 1:1.1 or less, 1:1.2 or less, 1:1.3 or less, 1:1.4 or less, 1:1.5 or less, 1:1.6 or less, 1:1.7 or less, 1:1.8 or less, 1:1.9 or less, 1:2 or less, 1:2.25 or less, 1:2.5 or less, 1:2.75 or less, 1:3 or less, 1:3.25 or less, 1:3.5 or less, 1:3.75 or less, 1:4 or less, 1:4.25 or less, 1:4.5 or less, 1:4.75 or less, 1:5 or less, 1:6 or less, 1:7 or less, 1:8 or less, 1:9 or less, 1:10 or less, 1:15 or less, 1:20 or less, 1:25 or less, 1:30 or less, 1:35 or less, 1:40 or less, 1:45 or less, 1:50 or less, 1:60 or less, 1:70 or less, 1:80 or less, 1:90 or less, 1:100 or less, 1:200 or less, 1:300 or less, 1:400 or less, 1:500 or less, 1:600 or less, or 1:700 or less).

The weight ratio of (a) a pyridine carboxylic acid herbicide or an agriculturally acceptable N-oxide, salt, or ester thereof to (b) dicamba, clopyralid, fluroxypyr, aminocyclopyrachlor, or an agriculturally acceptable salt or ester thereof can range from any of the minimum ratios described above to any of the maximum values described above. In some embodiments, the weight ratio of (a) a pyridine carboxylic acid herbicide or an agriculturally acceptable N-oxide, salt, or ester thereof to (b) dicamba or an agriculturally acceptable salt or ester thereof is from 1:800 to 6:1 (e.g., from 1:400 to 5:1, from 1:400 to 3:1, from 1:200 to 4:1, from 1:160 to 1:5, from 1:100 to 3:1, from 1:80 to 1:2.5, from 1:50 to 2:1, from 1:25 to 1:1, from 1:40 to 6:1, from 1:20 to 4:1, from 1:20 to 3:1, from 1:10 to 2:1, from 1:2 to 2:1 from 1:1.9 to 1.9:1, from 1:1.8 to 1.8:1, from 1:1.7 to 1.7:1, from 1:1.6 to 1.6:1, from 1:1.5 to 1.5:1, from 1:1.4 to 1.4:1, from 1:1.5 to 1.3:1, from 1:1.2 to 1.2:1, from 1:1.1 to 1.1:1, from 1:35 to 1:1, from 1:34 to 1:1, from 1:33 to 1:1, from 1:32 to 1:1, from 1:31 to 1:1, from 1:30 to 1:1, from 1:29 to 1:1, from 1:28 to 1:1, from 1:27 to 1:1, from 1:26 to 1:1, from 1:25 to 1:1, from 1:24 to 1:1, from 1:23 to 1:1, from 1:22 to 1:1, from 1:21 to 1:1, from 1:20 to 1:1, from 1:19 to 1:1, from 1:18 to 1:1, from 1:17 to 1:1, from 1:16 to 1:1, from 1:15 to 1:1, from 1:14 to 1:1, from 1:13 to 1:1, from 1:12 to 1:1, from 1:11 to 1:1, from 1:10 to 1:1, from 1:9 to 1:1, from 1:8 to 1:1, from 1:7 to 1:1, from 1:6 to 1:1, from 1:5 to 1:1, from 1:4 to 1:1, from 1:3 to 1:1, from 1:2 to 1:1, from 1:1.9 to 1:1, from 1:1.8 to 1:1, from 1:1.7 to 1:1, from 1:1.6 to 1:1, from 1:1.5 to 1:1, from 1:1.4 to 1:1, from 1:1.3 to 1:1, from 1:1.2 to 1:1, or from 1:1.1 to 1:1).

In some embodiments, (b) includes aminopyralid, halauxifen, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoro-2-pyridinecarboxylic acid, or an agriculturally acceptable salt or ester thereof. In some embodiments, the weight ratio of (a) a pyridine carboxylic acid herbicide or an agriculturally acceptable N-oxide, salt, or ester thereof to (b) aminopyralid, halauxifen, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoro-2-pyridinecarboxylic acid, or an agriculturally acceptable salt or ester thereof is 1:300 or more (e.g., 1:200 or more, 1:100 or more, 1:90 or more, 1:80 or more, 1:70 or more, 1:60 or more, 1:50 or more, 1:45 or more, 1:40 or more, 1:35 or more, 1:30 or more, 1:25 or more, 1:20 or more, 1:15 or more, 1:10 or more, 1:9 or more, 1:8 or more, 1:7 or more, 1:6 or more, 1:5 or more, 1:4.75 or more, 1:4.5 or more, 1:4.25 or more, 1:4 or more, 1:3.75 or more, 1:3.5 or more, 1:3.25 or more, 1:3 or more, 1:2.75 or more, 1:2.5 or more, 1:2.25 or more, 1:2 or more, 1:1.9 or more, 1:1.8 or more, 1:1.7 or more, 1:1.6 or more, 1:1.5 or more, 1:1.4 or more, 1:1.3 or more, 1:1.2 or more, 1:1.1 or more, 1:1 or more, 1.1:1 or more, 1.2:1 or more, 1.3:1 or more, 1.4:1 or more, 1.5:1 or more, 1.6:1 or more, 1.7:1 or more, 1.8:1 or more, 1.9:1 or more, 2:1 or more, 2.1:1 or more, 2.2:1 or more, 2.3:1 or more, 2.4:1 or more, 2.5:1 or more, 2.6:1 or more, 2.7:1 or more, 2.8:1 or more, 2.9:1 or more, 3:1 or more, 3.1:1 or more 3.2:1 or more, 3.3:1 or more, 3.4:1 or more, 3.5:1 or more, 3.6:1 or more, 3.7:1 or more, 3.8:1 or more, 3.9:1 or more, 4:1 or more, 4.1:1 or more, 4.2:1 or more, 4.3:1 or more, 4.4:1 or more, 4.5:1 or more, 4.6:1 or more, 4.7:1 or more, 4.8:1 or more, 4.9:1 or more, 5:1 or more, 6:1 or more, 7:1 or more, 8:1 or more, 9:1 or more, 10:1 or more, 15:1 or more, 20:1 or more, 25:1 or more, 30:1 or more, 35:1 or more, 40:1 or more, 50:1 or more, 60:1 or more, 70:1 or more, 80:1 or more, 90:1 or more, 100:1 or more, 120:1 or more, 140:1 or more, 160:1 or more, 180:1 or more, 200:1 or more, 220:1 or more, 240:1 or more, 260:1 or more, or 280:1 or more).

In some embodiments, the weight ratio of (a) a pyridine carboxylic acid herbicide or an agriculturally acceptable N-oxide, salt, or ester thereof to (b) aminopyralid, halauxifen, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoro-2-pyridinecarboxylic acid, or an agriculturally acceptable salt or ester thereof is 300:1 or less (e.g., 280:1 or less, 260:1 or less, 240:1 or less, 220:1 or less, 200:1 or less, 180:1 or less, 160:1 or less, 140:1 or less, 120:1 or less, 100:1 or less, 90:1 or less, 80:1 or less, 70:1 or less, 60:1 or less, 50:1 or less, 40:1 or less, 30:1 or less, 20:1 or less, 10:1 or less, 9:1 or less, 8:1 or less, 7:1 or less, 6:1 or less, 5:1 or less, 4.9:1 or less, 4.8:1 or less, 4.7:1 or less, 4.6:1 or less, 4.5:1 or less, 4.4:1 or less, 4.3:1 or less, 4.2:1 or less, 4.1:1 or less, 4:1 or less, 3.9:1 or less, 3.8:1 or less, 3.7:1 or less, 3.6:1 or less, 3.5:1 or less, 3.4:1 or less, 3.3:1 or less, 3.2:1 or less, 3.1:1 or less, 3:1 or less, 2.9:1 or less, 2.8:1 or less, 2.7:1 or less, 2.6:1 or less, 2.5:1 or less, 2.4:1 or less, 2.3:1 or less, 2.2:1 or less, 2.1:1 or less, 2:1 or less, 1.9:1 or less, 1.8:1 or less, 1.7:1 or less, 1.6:1 or less, 1.5:1 or less, 1.4:1 or less, 1.3:1 or less, 1.2:1 or less, 1.1:1 or less, 1:1 or less, 1:1.1 or less, 1:1.2 or less, 1:1.3 or less, 1:1.4 or less, 1:1.5 or less, 1:1.6 or less, 1:1.7 or less, 1:1.8 or less, 1:1.9 or less, 1:2 or less, 1:2.25 or less, 1:2.5 or less, 1:2.75 or less, 1:3 or less, 1:3.25 or less, 1:3.5 or less, 1:3.75 or less, 1:4 or less, 1:4.25 or less, 1:4.5 or less, 1:4.75 or less, 1:5 or less, 1:6 or less, 1:7 or less, 1:8 or less, 1:9 or less, 1:10 or less, 1:15 or less, 1:20 or less, 1:25 or less, 1:30 or less, 1:35 or less, 1:40 or less, 1:45 or less, 1:50 or less, 1:60 or less, 1:70 or less, 1:80 or less, 1:90 or less, 1:100 or less, or 1:200 or less).

The weight ratio of (a) a pyridine carboxylic acid herbicide or an agriculturally acceptable N-oxide, salt, or ester thereof to (b) aminopyralid, halauxifen, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoro-2-pyridinecarboxylic acid, or an agriculturally acceptable salt or ester thereof can range from any of the minimum ratios described above to any of the maximum values described above. In some embodiments, the weight ratio of (a) a pyridine carboxylic acid herbicide or an agriculturally acceptable N-oxide, salt, or ester thereof to (b) aminopyralid, halauxifen, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoro-2-pyridinecarboxylic acid, or an agriculturally acceptable salt or ester thereof is from 1:300 to 300:1 (e.g., from 1:300 to 5:1, from 1:250 to 250:1, from 1:200 to 200:1, from 1:150 to 150:1, from 1:100 to 100:1, from 1:50 to 50:1, from 1:25 to 25:1, from 1:10 to 10:1, from 1:60 to 1:1, from 1:40 to 5:1, from 1:30 to 4:1, from 1:20 to 3:1, from 1:10 to 2:1, from 1:5 to 5:1, from 1:4 to 4:1, from 1:3 to 3:1, from 1:2 to 2:1 from 1:1.9 to 1.9:1, from 1:1.8 to 1.8:1, from 1:1.7 to 1.7:1, from 1:1.6 to 1.6:1, from 1:1.5 to 1.5:1, from 1:1.4 to 1.4:1, from 1:1.5 to 1.3:1, from 1:1.2 to 1.2:1, from 1:1.1 to 1.1:1, from 1:35 to 1:1, from 1:34 to 1:1, from 1:33 to 1:1, from 1:32 to 1:1, from 1:31 to 1:1, from 1:30 to 1:1, from 1:29 to 1:1, from 1:28 to 1:1, from 1:27 to 1:1, from 1:26 to 1:1, from 1:25 to 1:1, from 1:24 to 1:1, from 1:23 to 1:1, from 1:22 to 1:1, from 1:21 to 1:1, from 1:20 to 1:1, from 1:19 to 1:1, from 1:18 to 1:1, from 1:17 to 1:1, from 1:16 to 1:1, from 1:15 to 1:1, from 1:14 to 1:1, from 1:13 to 1:1, from 1:12 to 1:1, from 1:11 to 1:1, from 1:10 to 1:1, from 1:9 to 1:1, from 1:8 to 1:1, from 1:7 to 1:1, from 1:6 to 1:1, from 1:5 to 1:1, from 1:4 to 1:1, from 1:3 to 1:1, from 1:2 to 1:1, from 1:1.9 to 1:1, from 1:1.8 to 1:1, from 1:1.7 to 1:1, from 1:1.6 to 1:1, from 1:1.5 to 1:1, from 1:1.4 to 1:1, from 1:1.3 to 1:1, from 1:1.2 to 1:1, or from 1:1.1 to 1:1).

In some embodiments, (b) includes quinclorac, picloram, triclopyr, or an agriculturally acceptable salt or ester thereof. In some embodiments, the weight ratio of (a) a pyridine carboxylic acid herbicide or an agriculturally acceptable N-oxide, salt, or ester thereof to (b) quinclorac, picloram, triclopyr, or an agriculturally acceptable salt or ester thereof is 1:4480 or more (e.g., 1:4400 or more, 1:4200 or more, 1:4000 or more, 1:3750 or more, 1:3500 or more, 1:3250:1 or more, 1:3000 or more, 1:2750 or more, 1:2500 or more, 1:2250 or more, 1:2000 or more, 1:1500 or more, 1:1000 or more, 1:750 or more, 1:500 or more, 1:400 or more, 1:300 or more, 1:200 or more, 1:100 or more, 1:90 or more, 1:80 or more, 1:70 or more, 1:60 or more, 1:50 or more, 1:45 or more, 1:40 or more, 1:35 or more, 1:30 or more, 1:25 or more, 1:20 or more, 1:15 or more, 1:10 or more, 1:9 or more, 1:8 or more, 1:7 or more, 1:6 or more, 1:5 or more, 1:4.75 or more, 1:4.5 or more, 1:4.25 or more, 1:4 or more, 1:3.75 or more, 1:3.5 or more, 1:3.25 or more, 1:3 or more, 1:2.75 or more, 1:2.5 or more, 1:2.25 or more, 1:2 or more, 1:1.9 or more, 1:1.8 or more, 1:1.7 or more, 1:1.6 or more, 1:1.5 or more, 1:1.4 or more, 1:1.3 or more, 1:1.2 or more, 1:1.1 or more, 1:1 or more, 1.1:1 or more, 1.2:1 or more, 1.3:1 or more, 1.4:1 or more, 1.5:1 or more, 1.6:1 or more, 1.7:1 or more, 1.8:1 or more, 1.9:1 or more, 2:1 or more, 2.1:1 or more, 2.2:1 or more, 2.25:1 or more, 2.3:1 or more, 2.4:1 or more, 2.5:1 or more, 2.6:1 or more, 2.7:1 or more, 2.75:1 or more, 2.8:1 or more, 2.9:1 or more, 3:1 or more, 3.1:1 or more 3.2:1 or more, 3.3:1 or more, 3.4:1 or more, 3.5:1 or more, 3.6:1 or more, 3.7:1 or more, 3.8:1 or more, 3.9:1 or more, 4:1 or more, 4.1:1 or more, 4.2:1 or more, 4.3:1 or more, 4.4:1 or more, 4.5:1 or more, 4.6:1 or more, 4.7:1 or more, 4.8:1 or more, 4.9:1 or more, 5:1 or more, 5.25:1 or more, 5.5:1 or more, 5.75:1 or more, 6:1 or more, 7:1 or more, 9:1 or more, 9:1 or more, 10:1 or more, 15:1 or more, 20:1 or more, 25:1 or more, or 30:1 or more).

In some embodiments, the weight ratio of (a) a pyridine carboxylic acid herbicide or an agriculturally acceptable N-oxide, salt, or ester thereof to (b) quinclorac, picloram, triclopyr, or an agriculturally acceptable salt or ester thereof is 30:1 or less (e.g., 25:1 or less, 20:1 or less, 15:1 or less, 10:1 or less, 9:1 or less, 8:1 or less, 7:1 or less, 6:1 or less, 5.75:1 or less, 5.5:1 or less, 5.25:1 or less, 5:1 or less, 4.9:1 or less, 4.8:1 or less, 4.7:1 or less, 4.6:1 or less, 4.5:1 or less, 4.4:1 or less, 4.3:1 or less, 4.2:1 or less, 4.1:1 or less, 4:1 or less, 3.9:1 or less, 3.8:1 or less, 3.7:1 or less, 3.6:1 or less, 3.5:1 or less, 3.4:1 or less, 3.3:1 or less, 3.2:1 or less, 3.1:1 or less, 3:1 or less, 2.9:1 or less, 2.8:1 or less, 2.75:1 or less, 2.7:1 or less, 2.6:1 or less, 2.5:1 or less, 2.4:1 or less, 2.3:1 or less, 2.25:1 or less, 2.2:1 or less, 2.1:1 or less, 2:1 or less, 1.9:1 or less, 1.8:1 or less, 1.7:1 or less, 1.6:1 or less, 1.5:1 or less, 1.4:1 or less, 1.3:1 or less, 1.2:1 or less, 1.1:1 or less, 1:1 or less, 1:1.1 or less, 1:1.2 or less, 1:1.3 or less, 1:1.4 or less, 1:1.5 or less, 1:1.6 or less, 1:1.7 or less, 1:1.8 or less, 1:1.9 or less, 1:2 or less, 1:2.25 or less, 1:2.5 or less, 1:2.75 or less, 1:3 or less, 1:3.25 or less, 1:3.5 or less, 1:3.75 or less, 1:4 or less, 1:4.25 or less, 1:4.5 or less, 1:4.75 or less, 1:5 or less, 1:6 or less, 1:7 or less, 1:8 or less, 1:9 or less, 1:10 or less, 1:15 or less, 1:20 or less, 1:25 or less, 1:30 or less, 1:35 or less, 1:40 or less, 1:45 or less, 1:50 or less, 1:60 or less, 1:70 or less, 1:80 or less, 1:90 or less, 1:100 or less, 1:200 or less, 1:300 or less, 1:400 or less, 1:500 or less, 1:750 or less, 1:1000 or less, 1:1500 or less, 1:2000 or less, 1:2250 or less, 1:2500 or less, 1:2750 or less, 1:3000 or less, 1:3250 or less, 1:3500 or less, 1:3750 or less, 1:4000 or less, 1:4200 or less, 1:4400 or less, or 1:4480 or less).

The weight ratio of (a) a pyridine carboxylic acid herbicide or an agriculturally acceptable N-oxide, salt, or ester thereof to (b) quinclorac, picloram, triclopyr, or an agriculturally acceptable salt or ester thereof can range from any of the minimum ratios described above to any of the maximum values described above. In some embodiments, the weight ratio of (a) a pyridine carboxylic acid herbicide or an agriculturally acceptable N-oxide, salt, or ester thereof to (b) quinclorac, picloram, triclopyr, or an agriculturally acceptable salt or ester thereof is from 1:4480 to 30:1 (e.g., from 1:4400 to 30:1, from 1:4000 to 27:1, from 1:3500 to 25:1, from 1:3000 to 20:1, from 1:2000 to 15:1, from 1:1000 to 10:1, from 1:750 to 7.5:1, from 1:500 to 5:1, 1:400 to 6:1, from 1:400 to 4:1, from 1:300 to 30:1, from 1:250 to 25:1, from 1:200 to 20:1, from 1:180 to 18:1, from 1:160 to 16:1, from 1:150 to 15:1, from 1:100 to 10:1, from 1:90 to 9:1, from 1:80 to 8:1, from 1:70 to 7:1, from 1:60 to 1:1, from 1:50 to 6:1, from 1:40 to 5:1, from 1:30 to 4:1, from 1:20 to 3:1, from 1:10 to 2:1, from 1:5 to 5:1, from 1:4 to 4:1, from 1:3 to 3:1, from 1:2 to 2:1 from 1:1.9 to 1.9:1, from 1:1.8 to 1.8:1, from 1:1.7 to 1.7:1, from 1:1.6 to 1.6:1, from 1:1.5 to 1.5:1, from 1:1.4 to 1.4:1, from 1:1.5 to 1.3:1, from 1:1.2 to 1.2:1, from 1:1.1 to 1.1:1, from 1:35 to 1:1, from 1:34 to 1:1, from 1:33 to 1:1, from 1:32 to 1:1, from 1:31 to 1:1, from 1:30 to 1:1, from 1:29 to 1:1, from 1:28 to 1:1, from 1:27 to 1:1, from 1:26 to 1:1, from 1:25 to 1:1, from 1:24 to 1:1, from 1:23 to 1:1, from 1:22 to 1:1, from 1:21 to 1:1, from 1:20 to 1:1, from 1:19 to 1:1, from 1:18 to 1:1, from 1:17 to 1:1, from 1:16 to 1:1, from 1:15 to 1:1, from 1:14 to 1:1, from 1:13 to 1:1, from 1:12 to 1:1, from 1:11 to 1:1, from 1:10 to 1:1, from 1:9 to 1:1, from 1:8 to 1:1, from 1:7 to 1:1, from 1:6 to 1:1, from 1:5 to 1:1, from 1:4 to 1:1, from 1:3 to 1:1, from 1:2 to 1:1, from 1:1.9 to 1:1, from 1:1.8 to 1:1, from 1:1.7 to 1:1, from 1:1.6 to 1:1, from 1:1.5 to 1:1, from 1:1.4 to 1:1, from 1:1.3 to 1:1, from 1:1.2 to 1:1, or from 1:1.1 to 1:1). In some embodiments, the active ingredients in the compositions disclosed herein consist of (a) a pyridine carboxylic acid herbicide or an agriculturally acceptable N-oxide, salt, or ester thereof and (b) a synthetic auxin herbicide or an agriculturally acceptable salt or ester thereof.

In some embodiments, the weight ratio of (a) a pyridine carboxylic acid herbicide or an agriculturally acceptable N-oxide, salt, or ester thereof in g ae/ha to (b) an auxin transport inhibitor, or an agriculturally acceptable salt or ester thereof in g ae/ha is 1:1000 or more (e.g., 1:900 or more, 1:800 or more, 1:700 or more, 1:600 or more, 1:500 or more, 1:400 or more, 1:300 or more, 1:200 or more, 1:100 or more, 1:90 or more, 1:80 or more, 1:70 or more, 1:60 or more, 1:50 or more, 1:45 or more, 1:40 or more, 1:35 or more, 1:30 or more, 1:25 or more, 1:20 or more, 1:15 or more, 1:10 or more, 1:9 or more, 1:8 or more, 1:7 or more, 1:6 or more, 1:5 or more, 1:4.75 or more, 1:4.5 or more, 1:4.25 or more, 1:4 or more, 1:3.75 or more, 1:3.5 or more, 1:3.25 or more, 1:3 or more, 1:2.75 or more, 1:2.5 or more, 1:2.25 or more, 1:2 or more, 1:1.9 or more, 1:1.8 or more, 1:1.7 or more, 1:1.6 or more, 1:1.5 or more, 1:1.4 or more, 1:1.3 or more, 1:1.2 or more, 1:1.1 or more, 1:1 or more, 1.1:1 or more, 1.2:1 or more, 1.3:1 or more, 1.4:1 or more, 1.5:1 or more, 1.6:1 or more, 1.7:1 or more, 1.8:1 or more, 1.9:1 or more, 2:1 or more, 2.25:1 or more, 2.5:1 or more, 2.75:1 or more, 3:1 or more, 3.25:1 or more, 3.5:1 or more, 3.75:1 or more, 4:1 or more, 4.25:1 or more, 4.5:1 or more, 4.75:1 or more, 5:1 or more, 6:1 or more, 7:1 or more, 8:1 or more, 9:1 or more, 10:1 or more, 15:1 or more, 20:1 or more, 25:1 or more, 30:1 or more, 35:1 or more, 40:1 or more, 45:1 or more, 50:1 or more, 55:1 or more, 60:1 or more, 65:1 or more, 70:1 or more, 75:1 or more, or 80:1 or more).

In some embodiments, the weight ratio of (a) a pyridine carboxylic acid herbicide or an agriculturally acceptable N-oxide, salt, or ester thereof in g ae/ha to (b) an auxin transport inhibitor, or an agriculturally acceptable salt or ester thereof in g ae/ha is 85:1 or less (e.g., 80:1 or less, 75:1 or less, 70:1 or less, 65:1 or less, 60:1 or less, 55:1 or less, 50:1 or less, 45:1 or less, 40:1 or less, 35:1 or less, 30:1 or less, 25:1 or less, 20:1 or less, 15:1 or less, 10:1 or less, 9:1 or less, 8:1 or less, 7:1 or less, 6:1 or less, 5:1 or less, 4.75:1 or less, 4.5:1 or less, 4.25:1 or less, 4:1 or less, 3.75:1 or less, 3.5:1 or less, 3.25:1 or less, 3:1 or less, 2.75:1 or less, 2.5:1 or less, 2.25:1 or less, 2:1 or less, 1.9:1 or less, 1.8:1 or less, 1.7:1 or less, 1.6:1 or less, 1.5:1 or less, 1.4:1 or less, 1.3:1 or less, 1.2:1 or less, 1.1:1 or less, 1:1 or less, 1:1.1 or less, 1:1.2 or less, 1:1.3 or less, 1:1.4 or less, 1:1.5 or less, 1:1.6 or less, 1:1.7 or less, 1:1.8 or less, 1:1.9 or less, 1:2 or less, 1:2.25 or less, 1:2.5 or less, 1:2.75 or less, 1:3 or less, 1:3.25 or less, 1:3.5 or less, 1:3.75 or less, 1:4 or less, 1:4.25 or less, 1:4.5 or less, 1:4.75 or less, 1:5 or less, 1:6 or less, 1:7 or less, 1:8 or less, 1:9 or less, 1:10 or less, 1:15 or less, 1:20 or less, 1:25 or less, 1:30 or less, 1:35 or less, 1:40 or less, 1:45 or less, 1:50 or less, 1:60 or less, 1:70 or less, 1:80 or less, 1:90 or less, 1:100 or less, 1:200 or less, 1:300 or less, 1:400 or less, 1:500 or less, 1:600 or less, 1:700 or less, 1:800 or less, or 1:900 or less).

The weight ratio of (a) a pyridine carboxylic acid herbicide or an agriculturally acceptable N-oxide, salt, or ester thereof in g ae/ha to (b) an auxin transport inhibitor, or an agriculturally acceptable salt or ester thereof in g ae/ha can range from any of the minimum ratios described above to any of the maximum values described above. For example, in some embodiments, the weight ratio of (a) a pyridine carboxylic acid herbicide or an agriculturally acceptable N-oxide, salt, or ester thereof in g ae/ha to (b) a auxin transport inhibitor, or an agriculturally acceptable salt or ester thereof in g ae/ha is from 1:1000 to 85:1 (e.g., 1:1000 to 20:1, from 1:900 to 10:1, from 1:800 to 9:1, from 1:700 to 8:1, from 1:600 to 8:1, from 1:500 to 8:1, from 1:400 to 8:1, from 1:300 to 8:1, from 1:900 to 50:1, from 1:800 to 40:1, from 1:700 to 30:1, from 1:600 to 20:1, from 1:500 to 15:1, from 1:400 to 10:1, from 1:300 to 9:1, from 1:200 to 12:1, from 1:100 to 12:1, from 1:50 to 12:1, from 1:20 to 12:1, from 1:10 to 12:1, from 1:2 to 12:1, from 1:1 to 12:1, from 1:2 to 6:1, from 1:1 to 6:1, from 1:100 to 7:1, from 1:50 to 6:1, from 1:40 to 5:1, from 1:30 to 4:1, from 1:20 to 3:1, from 1:10 to 2:1, from 1:5 to 5:1, from 1:4 to 4:1, from 1:3 to 3:1, from 1:2 to 2:1 from 1:1.9 to 1.9:1, from 1:1.8 to 1.8:1, from 1:1.7 to 1.7:1, from 1:1.6 to 1.6:1, from 1:1.5 to 1.5:1, from 1:1.4 to 1.4:1, from 1:1.3 to 1.3:1, from 1:1.2 to 1.2:1, from 1:1.1 to 1.1:1, from 1:35 to 1:1, from 1:34 to 1:1, from 1:33 to 1:1, from 1:32 to 1:1, from 1:31 to 1:1, from 1:30 to 1:1, from 1:29 to 1:1, from 1:28 to 1:1, from 1:27 to 1:1, from 1:26 to 1:1, from 1:25 to 1:1, from 1:24 to 1:1, from 1:23 to 1:1, from 1:22 to 1:1, from 1:21 to 1:1, from 1:20 to 1:1, from 1:19 to 1:1, from 1:18 to 1:1, from 1:17 to 1:1, from 1:16 to 1:1, from 1:15 to 1:1, from 1:14 to 1:1, from 1:13 to 1:1, from 1:12 to 1:1, from 1:11 to 1:1, from 1:10 to 1:1, from 1:9 to 1:1, from 1:8 to 1:1, from 1:7 to 1:1, from 1:6 to 1:1, from 1:5 to 1:1, from 1:4 to 1:1, from 1:3 to 1:1, from 1:2 to 1:1, from 1:1.9 to 1:1, from 1:1.8 to 1:1, from 1:1.7 to 1:1, from 1:1.6 to 1:1, from 1:1.5 to 1:1, from 1:1.4 to 1:1, from 1:1.3 to 1:1, from 1:1.2 to 1:1, or from 1:1.1 to 1:1).

In certain embodiments, the weight ratio of (a) a pyridine carboxylic acid herbicide or an agriculturally acceptable N-oxide, salt, or ester thereof in g ae/ha to (b) an auxin transport inhibitor, or an agriculturally acceptable salt or ester thereof in g ae/ha is from 1:200 to 12:1 (e.g., from 1:2 to 12:1, from 1:1 to 6:1, or from 1.25:1 to 5:1).

In some embodiments, the auxin transport inhibitor includes diflufenzopyr, naptalam, 2,3,5-triiodobenzoic acid, or an agriculturally acceptable salt or ester thereof.

In some examples, the active ingredients in the compositions disclosed herein consist of (a) a pyridine carboxylic acid herbicide or an agriculturally acceptable N-oxide, salt, or ester thereof and (b) an auxin transport inhibitor, or an agriculturally acceptable salt or ester thereof.

B. Formulations

The present disclosure also relates to formulations of the compositions and methods disclosed herein. In some embodiments, the formulation can be in the form of a single package formulation including both (a) a pyridine carboxylic acid herbicide or an agriculturally acceptable N-oxide, salt, or ester thereof and (b) a synthetic auxin herbicide, auxin transport inhibitor, agriculturally acceptable salts or esters thereof, or combinations thereof. In some embodiments, the formulation can be in the form of a single package formulation including both (a) and (b) and further including at least one additive. In some embodiments, the formulation can be in the form of a two-package formulation, wherein one package contains (a) and optionally at least one additive while the other package contains (b) and optionally at least one additive. In some embodiments of the two-package formulation, the formulation including (a) and optionally at least one additive and the formulation including (b) and optionally at least one additive are mixed before application and then applied simultaneously. In some embodiments, the mixing is performed as a tank mix (i.e., the formulations are mixed immediately before or upon dilution with water). In some embodiments, the formulation including (a) and the formulation including (b) are not mixed but are applied sequentially (in succession), for example, immediately or within 1 hour, within 2 hours, within 4 hours, within 8 hours, within 16 hours, within 24 hours, within 2 days, or within 3 days, of each other.

In some embodiments, the formulation of (a) and (b) is present in suspended, emulsified, or dissolved form. Exemplary formulations include, but are not limited to, aqueous solutions, powders, suspensions, also highly-concentrated aqueous, oily or other suspensions or dispersions, aqueous emulsions, aqueous microemulsions, aqueous suspo-emulsions, oil dispersions, self-emulsifying formulations, pastes, dusts, and materials for spreading or granules.

In some embodiments, (a) a pyridine carboxylic acid herbicide or an agriculturally acceptable N-oxide, salt, or ester thereof and/or (b) a synthetic auxin herbicide, auxin transport inhibitor, agriculturally acceptable salts or esters thereof, or combinations thereof is an aqueous solution that can be diluted before use. In some embodiments, (a) and/or (b) is provided as a high-strength formulation such as a concentrate. In some embodiments, the concentrate is stable and retains potency during storage and shipping. In some embodiments, the concentrate is a clear, homogeneous liquid that is stable at temperatures of 54° C. or greater. In some embodiments, the concentrate does not exhibit any precipitation of solids at temperatures of −10° C. or higher. In some embodiments, the concentrate does not exhibit separation, precipitation, or crystallization of any components at low temperatures. For example, the concentrate remains a clear solution at temperatures below 0° C. (e.g., below −5° C., below −10° C., below −15° C.). In some embodiments, the concentrate exhibits a viscosity of less than 50 centipoise (50 megapascals), even at temperatures as low as 5° C.

The compositions and methods disclosed herein can also be mixed with or applied with an additive. In some embodiments, the additive can be diluted in water or can be concentrated. In some embodiments, the additive is added sequentially. In some embodiments, the additive is added simultaneously. In some embodiments, the additive is premixed with the pyridine carboxylic acid herbicide or an agriculturally acceptable N-oxide, salt, or ester thereof. In some embodiments, the additive is premixed with the synthetic auxin herbicide, auxin transport inhibitor, agriculturally acceptable salts or esters thereof, or combinations thereof.

C. Other Actives

In some embodiments, the additive is an additional pesticide. For example, the compositions described herein can be applied in conjunction with one or more additional herbicides to control undesirable vegetation. The composition can be formulated with the one or more additional herbicides, tank mixed with the one or more additional herbicides, or applied sequentially with the one or more additional herbicides. Exemplary additional herbicides include, but are not limited to: acetochlor, acifluorfen, aclonifen, acrolein, alachlor, allidochlor, alloxydim, allyl alcohol, alorac, ametridione, ametryn, amibuzin, amicarbazone, amidosulfuron, amiprofos-methyl, amitrole, ammonium sulfamate, anilofos, anisuron, asulam, atraton, atrazine, azafenidin, aziprotryne, barban, BCPC, beflubutamid, benazolin, bencarbazone, benfluralin, benfuresate, bensulide, benthiocarb, bentazon-sodium, benzadox, benzfendizone, benzipram, benzobicyclon, benzofenap, benzofluor, benzoylprop, benzthiazuron, bicyclopyrone, bifenox, bilanafos, borax, bromacil, bromobonil, bromobutide, bromofenoxim, bromoxynil, brompyrazon, butachlor, butafenacil, butamifos, butenachlor, buthidazole, buthiuron, butralin, butroxydim, buturon, butylate, cacodylic acid, cafenstrole, calcium chlorate, calcium cyanamide, carbasulam, carbetamide, carboxazole, chlorprocarb, carfentrazone-ethyl, CDEA, CEPC, chlomethoxyfen, chloranocryl, chlorazifop, chlorazine, chlorbromuron, chlorbufam, chloreturon, chlorfenac, chlorfenprop, chlorflurazole, chlorflurenol, chloridazon, chlorimuron, chlormequat, chlomitrofen, chloropon, chlorotoluron, chloroxuron, chloroxynil, chlorpropham, chlorsulfuron, chlorthal, chlorthiamid, cinidon-ethyl, cinmethylin, cisanilide, clacyfos, clethodim, cliodinate, clodinafop, clofop, clomazone, cloproxydim, cloransulam-methyl, CMA, copper sulfate, CPMF, CPPC, credazine, cresol, cumyluron, cyanatryn, cyanazine, cycloate, cyclopyrimorate, cyclosulfamuron, cycloxydim, cycluron, cyhalofop, cyperquat, cyprazine, cyprazole, cypromid, daimuron, dalapon, dazomet, delachlor, desmedipham, desmetryn, di-allate, dichlobenil, dichloralurea, dichlormate, diclofop, diclosulam, diethamquat, diethatyl, difenopenten, difenoxuron, difenzoquat, diflufenican, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimexano, dimidazon, dinitramine, dinofenate, dinoprop, dinosam, dinoseb, dinoterb, diphenamid, dipropetryn, diquat, dithiopyr, diuron, DMPA, DNOC, DSMA, EBEP, eglinazine, endothal, epronaz, EPTC, esprocarb, ethalfluralin, ethbenzamide, ethametsulfuron, ethidimuron, ethiolate, ethobenzamid, etobenzamid, ethofumesate, ethoxyfen, etinofen, etobenzanid, EXD, fenasulam, isoxadifen-ethyl, fenoxaprop, fenoxaprop-P, fenoxasulfone, fenthiaprop, fenquinotrione, fentrazamide, fenuron, ferrous sulfate, flamprop, flamprop-M, fluazifop, fluazifop-P, fluazolate, flucarbazone, flucetosulfuron, fluchloralin, flufenacet, flufenican, flufenpyr-ethyl, flumetsulam, flumezin, flumiclorac-pentyl, flumioxazin, flumipropyn, fluometuron, fluorodifen, fluoroglycofen, fluoromidine, fluoronitrofen, fluothiuron, flupoxam, flupropacil, flupropanate, flupyrsulfuron, fluridone, flurochloridone, flurtamone, fluthiacet, fomesafen, foramsulfuron, fosamine, fumiclorac, furyloxyfen, glufosinate, glufosinate-ammonium, glufosinate-P-ammonium, glyphosate salts and esters, halosafen, haloxydine, haloxyfop, haloxyfop-P, hexachloroacetone, hexaflurate, hexazinone, IAA, IBA, imazamethabenz, imazapic, imazapyr, imazaquin, indanofan, indaziflam, iodobonil, iodomethane, iodosulfuron, iodosulfuron-ethyl-sodium, iofensulfuron, ioxynil, ipazine, ipfencarbazone, iprymidam, isocarbamid, isocil, isomethiozin, isonoruron, isopolinate, isopropalin, isoproturon, isouron, isoxaben, isoxachlortole, isoxaflutole, isoxpyrifop, karbutilate, ketospiradox, kuicaoxi, lactofen, lenacil, linuron, MAA, MAMA, medinoterb, mefenacet, mefluidide, mesoprazine, mesosulfuron, mesotrione, metam, metamifop, metamitron, metazachlor, metflurazon, methabenzthiazuron, methalpropalin, methazole, methiobencarb, methiozolin, methiuron, methometon, methoprotryne, methyl bromide, methyl isothiocyanate, methyldymron, metobenzuron, metobromuron, metolachlor, metosulam, metoxuron, metribuzin, molinate, monalide, monisouron, monochloroacetic acid, monolinuron, monuron, morfamquat, MSMA, naproanilide, napropamide, napropamide-M, neburon, nicosulfuron, nipyraclofen, nitralin, nitrofen, nitrofluorfen, norflurazon, noruron, orbencarb, ortho-dichlorobenzene, oryzalin, oxadiargyl, oxadiazon, oxapyrazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraflufen-ethyl, parafluron, paraquat, pebulate, pelargonic acid, pendimethalin, pentachlorophenol, pentanochlor, pentoxazone, perfluidone, pethoxamid, phenisopham, phenmedipham, phenmedipham-ethyl, phenobenzuron, phenylmercury acetate, picolinafen, pinoxaden, piperophos, potassium arsenite, potassium azide, potassium cyanate, pretilachlor, primisulfuron-methyl, procyazine, prodiamine, profluazol, profluralin, profoxydim, proglinazine, prohexadione-calcium, prometon, prometryn, pronamide, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone, propyzamide, prosulfalin, prosulfocarb, prosulfuron, proxan, prynachlor, pydanon, pyraclonil, pyraflufen-ethyl, pyrasulfotole, pyrazogyl, pyrazolynate, pyrazoxyfen, pyributicarb, pyriclor, pyridafol, pyridate, pyrithiobac-sodium, pyroxasulfone, quinclorac, quinmerac, quinoclamine, quinonamid, quizalofop, quizalofop-P, rhodethanil, rimsulfuron, saflufenacil, S-metolachlor, sebuthylazine, secbumeton, sethoxydim, siduron, simazine, simeton, simetryn, SMA, sodium arsenite, sodium azide, sodium chlorate, sulcotrione, sulfallate, sulfentrazone, sulfometuron, sulfosate, sulfosulfuron, sulfuric acid, sulglycapin, swep, TCA, tebutam, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbuchlor, terbumeton, terbuthylazine, terbutryn, tetrafluron, thenylchlor, thiameturon, thiazafluron, thiazopyr, thidiazimin, thidiazuron, thiencarbazone-methyl, thifensulfuron, thifensulfurn-methyl, thiobencarb, tiafenacil, tiocarbazil, tioclorim, tolpyralate, topramezone, tralkoxydim, tri-allate, triafamone, triasulfuron, triaziflam, tribenuron, tribenuron-methyl, tridiphane, trietazine, trifloxysulfuron, trifludimoxazin, trifluralin, triflusulfuron, trifop, trifopsime, trihydroxytriazine, trimeturon, tripropindan, tritac, tritosulfuron, vernolate, xylachlor, salts, esters, optically active isomers, and mixtures thereof.

In some embodiments, the additional pesticide or an agriculturally acceptable salt or ester thereof is provided in a premixed formulation with (a), (b), or combinations thereof. In some embodiments, the pyridine carboxylic acid herbicide or an agriculturally acceptable N-oxide, salt, or ester thereof is provided in a premixed formulation with an additional pesticide. In some embodiments, the synthetic auxin herbicide or an agriculturally acceptable salt or ester thereof is provided in a premixed formulation with an additional pesticide. In some embodiments, the auxin transport inhibitor or an agriculturally acceptable salt or ester thereof is provided in a premixed formulation with an additional pesticide.

D. Adjuvants/Carriers/Colorants/Adhesives

In some embodiments, the additive includes an agriculturally acceptable adjuvant. Exemplary agriculturally acceptable adjuvants include, but are not limited to, antifreeze agents, antifoam agents, compatibilizing agents, sequestering agents, neutralizing agents and buffers, corrosion inhibitors, colorants, odorants, penetration aids, wetting agents, spreading agents, dispersing agents, thickening agents, freeze point depressants, antimicrobial agents, crop oil, herbicide safeners, adhesives (for instance, for use in seed formulations), surfactants, protective colloids, emulsifiers, tackifiers, and mixtures thereof. Exemplary agriculturally acceptable adjuvants include, but are not limited to, crop oil concentrate (mineral oil (85%)+emulsifiers (15%)); nonylphenol ethoxylate; benzylcocoalkyldimethyl quaternary ammonium salt; blend of petroleum hydrocarbon, alkyl esters, organic acid, and anionic surfactant; C₉-C₁₁ alkylpolyglycoside; phosphate alcohol ethoxylate; natural primary alcohol (C₁₂-C₁₆) ethoxylate; di-sec-butylphenol EO-PO block copolymer; polysiloxane-methyl cap; nonylphenol ethoxylate+urea ammonium nitrate; emulsified methylated seed oil; tridecyl alcohol (synthetic) ethoxylate (8 EO); tallow amine ethoxylate (15 EO); and PEG(400) dioleate-99.

In some embodiments, the additive is a safener that is an organic compound leading to better crop plant compatibility when applied with a herbicide. In some embodiments, the safener itself is herbicidally active. In some, the safener acts as an antidote or antagonist in the crop plants and can reduce or prevent damage to the crop plants. Exemplary safeners include, but are not limited to, AD-67 (MON 4660), benoxacor, benthiocarb, brassinolide, cloquintocet (mexyl), cyometrinil, cyprosulfamide, daimuron, dichlormid, dicyclonon, dietholate, dimepiperate, disulfoton, fenchlorazole, fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim, furilazole, harpin proteins, isoxadifen-ethyl, jiecaowan, jiecaoxi, mefenpyr, mefenpyr-diethyl, mephenate, naphthalic anhydride, 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine, 4-(dichloroacetyl)-1-oxa-4-azaspiro [4.5]decane, oxabetrinil, R29148, and N-phenyl-sulfonylbenzoic acid amides, as well as thereof agriculturally acceptable salts and, provided they have a carboxyl group, their agriculturally acceptable derivatives. In some embodiments, the safener can be cloquintocet or an ester or salt or ester thereof, such as cloquintocet (mexyl). In some embodiments, the safener can be dichlormid. In some embodiments, the safener is employed in rice, cereal, or corn/maize. For example, dichlormid or cloquintocet can be used to antagonize harmful effects of the compositions on rice, row crops, and cereals.

Exemplary surfactants (e.g., wetting agents, tackifiers, dispersants, emulsifiers) include, but are not limited to, the alkali metal salts, alkaline earth metal salts and ammonium salts of aromatic sulfonic acids, for example lignosulfonic acids, phenolsulfonic acids, naphthalenesulfonic acids, and dibutylnaphthalenesulfonic acid, and of fatty acids, alkyl- and alkylarylsulfonates, alkyl sulfates, lauryl ether sulfates and fatty alcohol sulfates, and salts of sulfated hexa-, hepta- and octadecanols, and also of fatty alcohol glycol ethers, condensates of sulfonated naphthalene and its derivatives with formaldehyde, condensates of naphthalene or of the naphthalene sulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl-, octyl- or nonylphenol, alkylphenyl or tributylphenyl polyglycol ether, alkyl aryl polyether alcohols, isotridecyl alcohol, fatty alcohol/ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers or polyoxypropylene alkyl ethers, lauryl alcohol polyglycol ether acetate, sorbitol esters, lignosulfite waste liquors and proteins, denatured proteins, polysaccharides (e.g., methylcellulose), hydrophobically modified starches, polyvinyl alcohol, polycarboxylates, polyalkoxylates, polyvinyl amine, polyethyleneimine, polyvinylpyrrolidone and copolymers thereof.

Exemplary thickeners include, but are not limited to, polysaccharides, such as xanthan gum, and organic and inorganic sheet minerals, and mixtures thereof.

Exemplary antifoam agents include, but are not limited to, silicone emulsions, long-chain alcohols, fatty acids, salts of fatty acids, organofluorine compounds, and mixtures thereof.

Exemplary antimicrobial agents include, but are not limited to, bactericides based on dichlorophen and benzyl alcohol hemiformal, and isothiazolinone derivatives, such as alkylisothiazolinones and benzisothiazolinones, and mixtures thereof.

Exemplary antifreeze agents, include, but are not limited to ethylene glycol, propylene glycol, urea, glycerol, and mixtures thereof.

Exemplary colorants include, but are not limited to, the dyes known under the names Rhodamine B, pigment blue 15:4, pigment blue 15:3, pigment blue 15:2, pigment blue 15:1, pigment blue 80, pigment yellow 1, pigment yellow 13, pigment red 112, pigment red 48:2, pigment red 48:1, pigment red 57:1, pigment red 53:1, pigment orange 43, pigment orange 34, pigment orange 5, pigment green 36, pigment green 7, pigment white 6, pigment brown 25, basic violet 10, basic violet 49, acid red 51, acid red 52, acid red 14, acid blue 9, acid yellow 23, basic red 10, basic red 108, and mixtures thereof.

Exemplary adhesives include, but are not limited to, polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol, tylose, and mixtures thereof.

In some embodiments, the additive includes a carrier. In some embodiments, the additive includes a liquid or solid carrier. In some embodiments, the additive includes an organic or inorganic carrier. Exemplary liquid carriers include, but are not limited to, petroleum fractions or hydrocarbons such as mineral oil, aromatic solvents, paraffinic oils, and the like or less, vegetable oils such as soybean oil, rapeseed oil, olive oil, castor oil, sunflower seed oil, coconut oil, corn oil, cottonseed oil, linseed oil, palm oil, peanut oil, safflower oil, sesame oil, tung oil and the like or less, esters of the above vegetable oils or less, esters of monoalcohols or dihydric, trihydric, or other lower polyalcohols (4-6 hydroxy containing), such as 2-ethyl hexyl stearate, n-butyl oleate, isopropyl myristate, propylene glycol dioleate, di-octyl succinate, di-butyl adipate, di-octyl phthalate and the like or less, esters of mono-, di-, and polycarboxylic acids and the like, toluene, xylene, petroleum naphtha, crop oil, acetone, methyl ethyl ketone, cyclohexanone, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, propylene glycol monomethyl ether and diethylene glycol monomethyl ether, methyl alcohol, ethyl alcohol, isopropyl alcohol, amyl alcohol, ethylene glycol, propylene glycol, glycerine, N-methyl-2-pyrrolidinone, N,N-dimethyl alkylamides, dimethyl sulfoxide, liquid fertilizers and the like, and water as well as mixtures thereof. Exemplary solid carriers include, but are not limited to, silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, pyrophyllite clay, attapulgus clay, kieselguhr, calcium carbonate, bentonite clay, Fuller's earth, cottonseed hulls, wheat flour, soybean flour, pumice, wood flour, walnut shell flour, lignin, ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas, cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders, and mixtures thereof.

In some embodiments, emulsions, pastes or oil dispersions, can be prepared by homogenizing (a) and (b) in water by means of wetting agent, tackifier, dispersant or emulsifier.

In some embodiments, concentrates suitable for dilution with water are prepared, comprising (a), (b), a wetting agent, a tackifier, and a dispersant or emulsifier.

In some embodiments, powders or materials for spreading and dusts can be prepared by mixing or concomitant grinding of (a) and (b) and optionally a safener with a solid carrier.

In some embodiments, granules (e.g., coated granules, impregnated granules and homogeneous granules) can be prepared by binding the (a) and (b) to solid carriers.

The formulations disclosed herein can comprise a synergistic, herbicidally effective amount of (a) and (b). In some embodiments, the concentrations of (a) and (b) in the formulations can be varied. In some embodiments, the formulations comprise from 1% to 95% (e.g., from 5% to 95%, from 10% to 80%, from 20% to 70%, from 30% to 50%) by total weight of (a) and (b). In formulations designed to be employed as concentrates, (a) and (b) can be present in a concentration of from 0.1 to 98 weight percent (0.5 to 90 weight percent), based on the total weight of the formulation. Concentrates can be diluted with an inert carrier, such as water, prior to application. The diluted formulations applied to undesired vegetation or the locus of undesired vegetation can contain from 0.0006 to 8.0 weight percent of (a) and (b) (e.g., from 0.001 to 5.0 weight percent), based on the total weight of the diluted formulation.

In some embodiments, (a) and (b), independently, can be employed in a purity of from 90% to 100% (e.g., from 95% to 100%) according to nuclear magnetic resonance (NMR) spectrometry. In some embodiments, the concentrations of (a), (b), and additional pesticides in the formulations can be varied. In some embodiments, the formulations comprise from 1% to 95% (e.g., from 5% to 95%, from 10% to 80%, from 20% to 70%, from 30% to 50%) by total weight of (a), (b), and additional pesticides. In some embodiments, (a), (b), and additional pesticides, independently, can be employed in a purity of from 90% to 100% (e.g., from 95% to 100%) according to NMR spectrometry.

III. Methods of Use

The compositions disclosed herein can be applied in any known technique for applying herbicides. Exemplary application techniques include, but are not limited to, spraying, atomizing, dusting, spreading, or direct application into water (in-water). The method of application can vary depending on the intended purpose. In some embodiments, the method of application can be chosen to ensure the finest possible distribution of the compositions disclosed herein.

In some embodiments, a method of controlling undesirable vegetation which comprises contacting the vegetation or the locus thereof with or applying to the soil or water to prevent the emergence or growth of vegetation any of the compositions is disclosed herein.

The compositions disclosed herein can be applied pre-emergence (before the emergence of undesirable vegetation) or post-emergence (i.e., during and/or after emergence of the undesirable vegetation). If desired, the compositions can be applied as an in-water application.

When the compositions are used in crops, the compositions can be applied after seeding and before or after the emergence of the crop plants. In some embodiments, the compositions disclosed herein show good crop tolerance even when the crop has already emerged, and can be applied during or after the emergence of the crop plants. In some embodiments, when the compositions are used in crops, the compositions can be applied before seeding of the crop plants.

In some embodiments, the compositions disclosed herein are applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation by spraying (e.g., foliar spraying). In some embodiments, the spraying techniques use, for example, water as carrier and spray liquor rates of from 10 liters per hectare (L/ha) to 2000 L/ha (e.g., from 50 L/ha to 1000 L/ha, or from 100 to 500 L/ha). In some embodiments, the compositions disclosed herein are applied by the low-volume or the ultra-low-volume method, wherein the application is in the form of micro granules. In some embodiments, wherein the compositions disclosed herein are less well tolerated by certain crop plants, the compositions can be applied with the aid of the spray apparatus in such a way that they come into little contact, if any, with the leaves of the sensitive crop plants while reaching the leaves of undesirable vegetation that grows underneath or the bare soil (e.g., post-directed or lay-by). In some embodiments, the compositions disclosed herein can be applied as dry formulations (e.g., granules, WDGs, etc.) into water.

In some embodiments, herbicidal activity is exhibited by the compounds of the mixture when they are applied directly to the plant or to the locus of the plant at any stage of growth or before planting or emergence. The effect observed can depend upon the type of undesirable vegetation to be controlled, the stage of growth of the undesirable vegetation, the application parameters of dilution and spray drop size, the particle size of solid components, the environmental conditions at the time of use, the specific compound employed, the specific adjuvants and carriers employed, the soil type, and the like, as well as the amount of chemical applied. In some embodiments, these and other factors can be adjusted to promote non-selective or selective herbicidal action. In some cases, the compositions are applied to relatively immature undesirable vegetation.

The compositions and methods disclosed herein can be used to control undesired vegetation in a variety of crop and non-crop applications. In some embodiments, the compositions and methods disclosed herein can be used for controlling undesired vegetation in crops. Exemplary crops include, but are not limited to, wheat, barley, triticale, rye, teff, oats, corn/maize, cotton, soy, sorghum, rice, sugarcane and range land (e.g., pasture grasses). In some embodiments, the undesirable vegetation is controlled in a row crop (e.g., corn/maize, sorghum, soybean, sunflower, sugarbeet, cotton, or spring rape/canola). In some embodiments, the compositions and methods disclosed herein can be used for controlling undesired vegetation in corn/maize, wheat, or a combination thereof.

The compositions and methods disclosed herein can be used for controlling undesired vegetation in non-crop areas. Exemplary non-crop areas include, but are not limited to, turfgrass, pastures, grasslands, rangelands, fallow land, rights-of-way, aquatic settings, tree and vine, wildlife management areas, or rangeland. In some embodiments, the compositions and methods disclosed herein can be used in industrial vegetation management (IVM) or for utility, pipeline, roadside, and railroad rights-of-way applications. In some embodiments, the compositions and methods disclosed herein can also be used in forestry (e.g., for site preparation or for combating undesirable vegetation in plantation forests). In some embodiments, the compositions and methods disclosed herein can be used to control undesirable vegetation in conservation reserve program lands (CRP), trees, vines, grasslands, and grasses grown for seeds. In some embodiments, the compositions and methods disclosed herein can be used on lawns (e.g., residential, industrial, and institutional), golf courses, parks, cemeteries, athletic fields, and sod farms.

The compositions and methods disclosed herein can also be used in crop plants that are resistant to, for instance, herbicides, pathogens, and/or insects. In some embodiments, the compositions and methods disclosed herein can be used in crop plants that are resistant to one or more herbicides because of genetic engineering or breeding. In some embodiments, the compositions and methods disclosed herein can be used in crop plants that are resistant to one or more pathogens such as plant pathogenous fungi owing to genetic engineering or breeding. In some embodiments, the compositions and methods disclosed herein can be used in crop plants that are resistant to attack by insects owing to genetic engineering or breeding. Exemplary resistant crops include, but are not limited to, crops that are resistant to photosystem II inhibitors, or crop plants that, owing to introduction of the gene for Bacillus thuringiensis (or Bt) toxin by genetic modification, are resistant to attack by certain insects. In some embodiments, the compositions and methods described herein also can be used in conjunction with glyphosate, glufosinate, aryloxyphenoxypropionates, acetyl CoA carboxylase (ACCase) inhibitors, imidazolinones, acetolactate synthase (ALS) inhibitors, 4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitors, protoporphyrinogen oxidase (PPO) inhibitors, triazines, and bromoxynil to control vegetation in crops tolerant to glyphosate, glufosinate, aryloxyphenoxypropionates, acetyl CoA carboxylase (ACCase) inhibitors, imidazolinones, acetolactate synthase (ALS) inhibitors, 4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitors, protoporphyrinogen oxidase (PPO) inhibitors, triazines, bromoxynil, or combinations thereof. In some embodiments, the undesirable vegetation is controlled in glyphosate, glufosinate, aryloxyphenoxypropionates, acetyl CoA carboxylase (ACCase) inhibitors, imidazolinones, acetolactate synthase (ALS) inhibitors, 4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitors, protoporphyrinogen oxidase (PPO) inhibitors, triazines, and bromoxynil tolerant crops possessing single, multiple or stacked traits conferring tolerance to single or multiple chemistries and/or multiple modes of action. In some embodiments, the undesirable vegetation can be controlled in a crop that is ACCase-tolerant, ALS-tolerant, or a combination thereof. The combination of (a), (b), and a complementary herbicide or salt or ester thereof can be used in combination with herbicides that are selective for the crop being treated and which complement the spectrum of weeds controlled by these compounds at the application rate employed. In some embodiments, the compositions described herein and other complementary herbicides are applied at the same time, either as a combination formulation or as a tank mix, or as sequential applications.

The compositions and methods may be used in controlling undesirable vegetation in crops possessing agronomic stress tolerance (including but not limited to drought, cold, heat, salt, water, nutrient, fertility, pH), pest tolerance (including but not limited to insects, fungi and pathogens) and crop improvement traits (including but not limited to yield; protein, carbohydrate, or oil content; protein, carbohydrate, or oil composition; plant stature and plant architecture).

In some embodiments, the compositions disclosed herein can be used for controlling undesirable vegetation including grasses, broadleaf weeds, sedge weeds, and combinations thereof. In some embodiments, the compositions disclosed herein can be used for controlling undesirable vegetation including, but not limited to, Polygonum species such as wild buckwheat (Polygonum convolvulus), Amaranthus species such as pigweed (Amaranthus retroflexus), Chenopodium species such as common lambsquarters (Chenopodium album L.), Sida species such as prickly sida (Sida spinosa L.), Ambrosia species such as common ragweed (Ambrosia artemisiifolia), Cyperus species such as nutsedge (Cyperus esculentus), Setaria species such as giant foxtail (Setariafaberi), Sorghum species, Acanthospermum species, Anthemis species, Atriplex species, Brassica species, Cirsium species, Convolvulus species, Conyza species, such as horseweed (Conyza canadensis), Cassia species, Commelina species, Datura species, Euphorbia species, Geranium species, Galinsoga species, Ipomea species such as morning-glory, Lamium species, Malva species, Matricaria species, Persicaria species, Prosopis species, Rumex species, Sisymbrium species, Solanum species, Trifolium species, Xanthium species, Veronica species, Viola species such as wild pansy (Viola tricolor), common chickweed (Stellaria media), velvetleaf (Abutilon theophrasti), hemp sesbania (Sesbania exaltata Cory), Anoda cristata, Bidens pilosa, Brassica kaber, shepherd's purse (Capsella bursa-pastoris), cornflower (Centaurea cyanus or Cyanus segetum), hempnettle (Galeopsis tetrahit), cleavers (Galium aparine), Helianthus annuus, Desmodium tortuosum, kochia (Kochia scoparia), Medicago arabica, Mercurialis annua, Myosotis arvensis, common poppy (Papaver rhoeas), Raphanus raphanistrum, Russian thistle (Salsola kali or Salsola iberica), wild mustard (Sinapis arvensis), Sonchus arvensis, Thlaspi arvense, Tagetes minuta, Richardia brasiliensis, Plantago major, Plantago lanceolata, bird's-eye speedwell (Veronica persica) and speedwell.

In some embodiments, the undesirable vegetation includes velvetleaf (Abutilon theophrasti, ABUTH), blackgrass (Alopecurus myosuroides, ALOMY), pigweed (Amaranthus retroflexus, AMARE), wild oat (Avenafatua, AVEFA), Chinese kale (Brassica alboglabra, BRSAG), brown mustard (Brassica juncea, BRSJU), rutabaga (Brassica napus var. napobrassica, BRSNA), black mustard (Brassica nigra, BRSNI), spring rape (Brassica napus, BRSNN), spring rape—Roundup Ready (Brassica napus, BRSNN-RR), winter rape (Brassica napus, BRSNW), turnip (Brassica rapa, BRSRR), common lambsquarters (Chenopodium album L., CHEAL), Canadian thistle (Cirsium arvense, CIRAR), nutsedge (Cyperus esculentus, CYPES), large crabgrass (Digitaria sanguinalis, DIGSA), barnyardgrass (Echinochloa crus-galli, ECHCG), poinsettia (Euphorbia heterophylla, EPHHL), soybean (Glycine max, GLXMA), sunflower (Helianthus annus, HELAN), ivyleaf morningglory (Ipomoea hederacea, IPOHE), kochia (Kochia scoparia, KCHSC), mallow (Malva pusilla, MALPU), wild buckwheat (Polygonum convolvulus, POLCO), lady's-thumb (Polygonum persicaria, POLPE), wild radish (Raphanus raphanistrum, RAPRA), Russian thistle (Salsola iberica, SASKR), wild mustard (Sinapsis arvensis, SINAR), grain sorghum (Sorghum vulgare, SORVU), Indian hedge mustard (Sisymbrium orientale, SSYOR), common chickweed (Stellaria media, STEME), ivyleaved speedwell (Veronica hederifolia, VERHE) and wild pansy (Viola tricolor, VIOTR), or a combination thereof.

In some embodiments, the undesirable vegetation includes velvetleaf (Abutilon theophrasti, ABUTH), pigweed (AMARE, Amaranthus retroflexus), spring rape (Brassica napus, BRSNN), winter rape (BRSNW, Brassica napus), common lambsquarters (CHEAL, Chenopodium album L.), Canadian thistle (CIRAR, Cirsium arvense), nutsedge (Cyperus esculentus, CYPES), poinsettia (Euphorbia heterophylla, EPHHL), sunflower (Helianthus annus, HELAN), kochia (KCHSC, Kochia scoparia), mallow (MALPU, Malva pusilla), wild buckwheat (POLCO, Polygonum convolvulus), lady's thumb (POLPE, Polygonum persicaria), grain sorghum (Sorghum vulgare, SORVU), common chickweed (Stellaria media, STEME), and wild pansy (Viola tricolor, VIOTR), or a combination thereof.

The herbicidal compositions described herein can be used to control herbicide resistant or tolerant weeds. The methods employing the compositions described herein may also be employed to control herbicide resistant or tolerant weeds. Exemplary resistant or tolerant weeds include, but are not limited to, biotypes resistant or tolerant to acetolactate synthase (ALS) or acetohydroxy acid synthase (AHAS) inhibitors (e.g., imidazolinones, sulfonylureas, pyrimidinylthiobenzoates, triazolopyrimidines, sulfonylaminocarbonyltriazolinones), photosystem II inhibitors (e.g., phenylcarbamates, pyridazinones, triazines, triazinones, uracils, amides, ureas, benzothiadiazinones, nitriles, phenylpyridazines), acetyl CoA carboxylase (ACCase) inhibitors (e.g., aryloxyphenoxypropionates, cyclohexanediones, phenylpyrazolines), auxin transport inhibitors (e.g., phthalamates, semicarbazones), photosystem I inhibitors (e.g., bipyridyliums), 5-enolpyruvylshikimate-3-phosphate (EPSP) synthase inhibitors (e.g., glyphosate), glutamine synthetase inhibitors (e.g., glufosinate, bialafos), microtubule assembly inhibitors (e.g., benzamides, benzoic acids, dinitroanilines, phosphoramidates, pyridines), mitosis inhibitors (e.g., carbamates), very long chain fatty acid (VLCFA) inhibitors (e.g., acetamides, chloroacetamides, oxyacetamides, tetrazolinones), fatty acid and lipid synthesis inhibitors (e.g., phosphorodithioates, thiocarbamates, benzofuranes, chlorocarbonic acids), protoporphyrinogen oxidase (PPO) inhibitors (e.g., diphenylethers, N-phenylphthalimides, oxadiazoles, oxazolidinediones, phenylpyrazoles, pyrimidinediones, thiadiazoles, triazolinones), carotenoid biosynthesis inhibitors (e.g., clomazone, amitrole, aclonifen), phytoene desaturase (PDS) inhibitors (e.g., amides, anilidex, furanones, phenoxybutan-amides, pyridiazinones, pyridines), 4-hydroxyphenyl-pyruvate-dioxygenase (HPPD) inhibitors (e.g., callistemones, isoxazoles, pyrazoles, triketones), cellulose biosynthesis inhibitors (e.g., nitriles, benzamides, quinclorac, triazolocarboxamides), herbicides with multiple modes-of-action such as quinclorac, and unclassified herbicides such as arylaminopropionic acids, difenzoquat, endothall, and organoarsenicals. Exemplary resistant or tolerant weeds include, but are not limited to, biotypes with resistance or tolerance to multiple herbicides, biotypes with resistance or tolerance to multiple chemical classes, biotypes with resistance or tolerance to multiple herbicide modes-of-action, and biotypes with multiple resistance or tolerance mechanisms (e.g., target site resistance or metabolic resistance).

By way of non-limiting illustration, examples of certain embodiments of the present disclosure are given below.

EXAMPLES Example 1—Greenhouse Trials

Methodology—Evaluation of Postemergence Herbicidal Activity in Crops

Seeds of the desired test plant species were planted in Sun Gro MetroMix® 306 planting mixture, which typically has a pH of 6.0 to 6.8 and an organic matter content of about 30 percent, in plastic pots with a surface area of 103.2 square centimeters (cm²). When required to ensure good germination and healthy plants, a fungicide treatment and/or other chemical or physical treatment was applied. The plants were grown for 7-36 days (d) in a greenhouse with an approximate 14-hour (h) photoperiod which was maintained at about 23° C. during the day and 22° C. during the night. Nutrients and water were added on a regular basis and supplemental lighting was provided with overhead metal halide 1000-Watt lamps as necessary. The plants were employed for testing when they reached the second or third true leaf stage.

Weighed amounts of technical or experimental material were dissolved in a volume of 97:3 volume per volume (v/v) acetone/dimethyl sulfoxide (DMSO) to stock solutions. If the compound did not dissolve readily, the mixture was warmed and/or sonicated. The concentrated stock solutions were diluted with an aqueous mixture of 1.5% v/v of Agri-dex crop oil concentrate to provide the appropriate application rates. Compound requirements are based upon a 12 milliliter (mL) application volume at a rate of 187 liters per hectare (L/ha). Stock solutions of the formulated materials were prepared following the same procedure. Spray solutions of the synthetic auxins or auxin transport inhibitors and experimental compound mixtures were prepared by adding the stock solutions to the appropriate amount of dilution solution to form a 12 mL spray solution in two-way combinations. Formulated compounds were applied to the plant material with an overhead Mandel track sprayer equipped with 8002E nozzles calibrated to deliver 187 L/ha over an application area of 0.503 square meters (m²) at a spray height of 18 inches (43 centimeters (cm)) above average plant canopy. Control plants were sprayed in the same manner with the solvent blank.

The treated plants and control plants were placed in a greenhouse as described above and watered by sub-irrigation to prevent wash-off of the test compounds. After 20-22 d, the condition of the test plants as compared with that of the control plants was determined visually and scored on a scale of 0 to 100 percent where 0 corresponds to no injury and 100 corresponds to complete kill. The condition of the test plants was compared with that of the control plants as determined visually and scored on a scale of 0 to 100 percent, where 0 corresponds to no injury and 100 corresponds to complete kill. Colby's equation was used to determine the herbicidal effects expected from the mixtures.

Compound 7 (soluble concentrate (SL) formulation) was combined with 2,4 D EHE (emulsifiable concentrate (EC)), MCPA EHE, Dichlorprop-P (as the potassium salt), mecoprop-P (as the potassium salt), dicamba-dimethylammonium (DMA) salt (as Banvel® 4S), clopyralid (as Lontrel™ 35A Herbicidal Concentrate), and fluroxypyr-MHE (EC) and applied to spring barley (HORVS), and winter wheat (TRZAW) and the phytotoxicity of the herbicidal compositions were measured. In addition, the efficacy of the herbicidal composition on pigweed (AMARE, Amaranthus retroflexus), winter rape (BRSNW, Brassica napus), common lambsquarters (CHEAL, Chenopodium album L.), Canadian thistle (CIRAR, Cirsium arvense), and kochia (KCHSC, Kochia scoparia) was evaluated. The results are summarized in Tables 1-7.

TABLE 1 Effect (% visual injury) of compound 7 and 2,4-D EHE on cereal weeds, spring barley (HORVS), and winter wheat (TRZAW). Application rate (g ae/ha) compound 7 8.75 0 8.75 2,4-D EHE 0 280 280 AMARE Obs 70 30 95 Exp — — 79 Δ 16 BRSNW Obs 58 85 100 Exp — — 94 Δ 6 CIRAR Obs 25 73 88 Exp — — 79 Δ 8 KCHSC Obs 55 10 73 Exp — — 60 Δ 13 HORVS Obs  0  0 0 Exp — — 0 Δ 0 TRZAW Obs  0  5 0 Exp — — 5 Δ −5 g ae/ha = grams acid equivalent per hectare; 2,4-D EHE = 2-ethylhexyl (2,4-dichlorophenoxy)acetate; AMARE = Amaranthus retroflexus (pigweed); BRSNW = Brassica napus (winter rape); CIRAR = Cirsium arvense (Canadian thistle); KCHSC = Kochia scoparia (kochia); HORVS = Hordeum vulgare (spring barley); TRZAW = Triticum aestivum (winter wheat)

TABLE 2 Effect (% visual injury) of compound 7 and MCPA EHE on cereal weeds. Application rate (g ae/ha) compound 7 8.75 0 8.75 MCPA EHE 0 280 280 AMARE Obs 70 35 84 Exp — — 81 Δ 4 BRSNW Obs 58 73 98 Exp — — 88 Δ 9 CHEAL Obs 60 75 94 Exp — — 90 Δ 4 KCHSC Obs 55  0 78 Exp — — 55 Δ 23 HORVS Obs  0  0 0 Exp — — 0 Δ 0 TRZAW Obs  0  3 0 Exp — — 3 Δ −3 g ae/ha = grams acid equivalent per hectare MCPA EHE = 2-ethylhexyl (4-chloro-2-methylphenoxy)acetate AMARE = Amaranthus retroflexus (pigweed) BRSNW = Brassica napus (winter rape) CHEAL = Chenopodium album L. (common lambsquarters) KCHSC = Kochia scoparia (kochia) HORVS = Hordeum vulgare (spring barley) TRZAW = Triticum aestivum (winter wheat)

TABLE 3 Effect (% visual injury) of compound 7 and Dichlorprop-P on cereal weeds. Application rate (g ae/ha) compound 7 8.75 0 8.75 Dichlorprop-P 0 280 280 AMARE Obs 70 40 100 Exp — — 82 Δ 18 BRSNW Obs 58 83 97 Exp — — 93 Δ 4 CIRAR Obs 25 75 85 Exp — — 81 Δ 4 HORVS Obs  0  0 0 Exp — — 0 Δ 0 TRZAW Obs  0  0 0 Exp — — 0 Δ 0 g ae/ha = grams acid equivalent per hectare AMARE = Amaranthus retroflexus (pigweed) BRSNW = Brassica napus (winter rape) CIRAR = Cirsium arvense (Canadian thistle) HORVS = Hordeum vulgare (spring barley) TRZAW = Triticum aestivum (winter wheat)

TABLE 4 Effect (% visual injury) of compound 7 and mecoprop-P on cereal weeds. Application rate (g ae/ha) compound 7 8.75 0 8.75 Mecoprop-P 0 400 400 AMARE Obs 70 58 99 Exp — — 87 Δ 11 BRSNW Obs 58 88 98 Exp — — 95 Δ 3 HORVS Obs  0  0 0 Exp — — 0 Δ 0 TRZAW Obs  0  0 0 Exp — — 0 Δ 0 g ae/ha = grams acid equivalent per hectare AMARE = Amaranthus retroflexus (pigweed) BRSNW = Brassica napus (winter rape) HORVS = Hordeum vulgare (spring barley) TRZAW = Triticum aestivum (winter wheat)

TABLE 5 Effect (% visual injury) of compound 7 and dicamba-DMA on cereal weeds. Application rate (g ae/ha) compound 7 8.75 0 8.75 Dicamba-DMA 0 140 140 AMARE Obs 70 67 98 Exp — — 90 Δ 7 BRSNW Obs 58 40 84 Exp — — 75 Δ 9 HORVS Obs  0  0 0 Exp — — 0 Δ 0 TRZAW Obs  0  0 0 Exp — — 0 Δ 0 g ae/ha = grams acid equivalent per hectare AMARE = Amaranthus retroflexus (pigweed) BRSNW = Brassica napus (winter rape) HORVS = Hordeum vulgare (spring barley) TRZAW = Triticum aestivum (winter wheat)

TABLE 6 Effect (% visual injury) of compound 7 and clopyralid on cereal weeds. Application rate (g ae/ha) compound 7 8.75 0 8.75 clopyralid 0 100 100 AMARE Obs 70 3 89 Exp — — 71 Δ 18 BRSNW Obs 58 0 80 Exp — — 58 Δ 23 CHEAL Obs 60 0 85 Exp — — 60 Δ 25 CIRAR Obs 25 85  93 Exp — — 89 Δ 4 HORVS Obs  0 5 0 Exp — — 5 Δ −5 TRZAW Obs  0 3 0 Exp — — 3 Δ −3 g ae/ha = grams acid equivalent per hectare AMARE = Amaranthus retroflexus (pigweed) BRSNW = Brassica napus (winter rape) CHEAL = Chenopodium album L. (common lambsquarters) CIRAR = Cirsium arvense (Canadian thistle) HORVS = Hordeum vulgare (spring barley) TRZAW = Triticum aestivum (winter wheat)

TABLE 7 Effect (% visual injury) of compound 7 and fluroxypyr-MHE on cereal weeds. Application rate compound 7 5 10 0 5 10 (g ae/ha) Fluroxypyr-MHE 0 0 70 70 70 CHEAL Obs 80 100 10 97 100 Exp — — — 82 100 Δ 15 0 CIRAR Obs 50 65 10 70 85 Exp — — — 55 69 Δ 15 17 HORVS Obs 0 15 20 10 25 Exp — — — 20 32 Δ −10 −7 g ae/ha = grams acid equivalent per hectare fluroxypyr-MHE = fluroxypyr methylheptyl ester = fluroxypyr-meptyl CHEAL = Chenopodium album L. (common lambsquarters) CIRAR = Cirsium arvense (Canadian thistle) HORVS = Hordeum vulgare (spring barley)

Example 2—Patio Trials

Methodology—Evaluation of Postemergence Herbicidal Activity in Crops

Seeds of the desired test plant species were planted in Sun Gro MetroMix® 306 planting mix, which typically has a pH of 6.0 to 6.8 and an organic matter content of about 30 percent, in plastic pots with a surface area of 103.2 square centimeters (cm²). When required to ensure good germination and healthy plants, a fungicide treatment and/or other chemical or physical treatment was applied to the seeds. The plants were grown for 7-36 days (d) on a fenced, open-air patio. Nutrients and water were added on a regular basis. The plants were employed for testing when they reached the second or third true leaf stage.

Weighed amounts of technical or experimental material were dissolved in a volume of 97:3 volume per volume (v/v) acetone/dimethyl sulfoxide (DMSO) to stock solutions. If the compound did not dissolve readily, the mixture was warmed and/or sonicated. The concentrated stock solutions were diluted with an aqueous mixture of 1.5% v/v of Agri-dex crop oil concentrate to provide the appropriate application rates. Compound requirements are based upon a 12 milliliter (mL) application volume at a rate of 187 liters per hectare (L/ha). Stock solutions of the formulated materials were prepared following the same procedure. Spray solutions of the synthetic auxins or auxin transport inhibitors and experimental compound mixtures were prepared by adding the stock solutions to the appropriate amount of dilution solution to form a 12 mL spray solution in two-way combinations. Formulated compounds were applied to the plant material with an overhead Mandel track sprayer equipped with 8002E nozzles calibrated to deliver 187 L/ha over an application area of 0.503 square meters (m²) at a spray height of 18 inches (43 centimeters (cm)) above average plant canopy. Control plants were sprayed in the same manner with the solvent blank.

The treated plants and control plants were placed back on the patio and watered by sub-irrigation to prevent wash-off of the test compounds. Temperatures and photoperiods were dependent on the natural weather conditions during the trials. Weather conditions during trials were conducive for plant growth and development. After 20-22 d, the condition of the test plants as compared with that of the control plants was determined visually and scored on a scale of 0 to 100 percent where 0 corresponds to no injury and 100 corresponds to complete kill. The condition of the test plants was compared with that of the control plants as determined visually and scored on a scale of 0 to 100 percent, where 0 corresponds to no injury and 100 corresponds to complete kill. Colby's equation was used to determine the herbicidal effects expected from the mixtures.

Compound 7 (SL) was combined with 2,4 D EHE (EC), MCPA EHE, and halauxifen-methyl (as Arylex™; suspension concentrate (SC)) and applied to winter wheat (TRZAW) and the phytotoxicity of the herbicidal compositions were measured. In addition, the efficacy of the herbicidal composition on pigweed (AMARE, Amaranthus retroflexus) and kochia (KCHSC, Kochia scoparia) was evaluated. The results are summarized in Tables 8-10.

TABLE 8 Effect (% visual injury) of compound 7 and halauxifen-methyl on cereal weeds. Application rate (g ae/ha) compound 7 8.75 0 8.75 halauxifen-methyl 0 8.75 8.75 KCHSC Obs 5 60 73 Exp — — 62 Δ 11 TRZAW Obs 5 10 8 Exp — — 15 Δ −7 g ae/ha = grams acid equivalent per hectare KCHSC = Kochia scoparia (kochia) TRZAW = Triticum aestivum (winter wheat)

TABLE 9 Effect (% visual injury) of compound 7 and 2,4-D EHE on cereal weeds. Application compound 7 8.75 17.5 0 8.75 17.5 rate (g ae/ha) 2,4-D EHE 0 0 280 280 280 AMARE Obs 30 40 50 100 100 Exp — — — 65 70 Δ 35 30 KCHSC Obs 5 0 10 20 60 Exp — — — 15 10 Δ 6 50 g ae/ha = grams acid equivalent per hectare 2,4-D EHE = 2-ethylhexyl (2,4-dichlorophenoxy)acetate AMARE = Amaranthus retroflexus (pigweed) KCHSC = Kochia scoparia (kochia)

TABLE 10 Effect (% visual injury) of compound 7 and MCPA EHE on cereal weeds. Application rate compound 7 8.75 17.5 0 8.75 17.5 (g ae/ha) MCPA EHE 0 0 280 280 280 KCHSC Obs 5 0 20 60 30 Exp — — — 24 20 Δ 36 10 TRZAW Obs 5 0 0 5 0 Exp — — — 5 0 Δ 0 0 g ae/ha = grams acid equivalent per hectare MCPA EHE = 2-ethylhexyl (4-chloro-2-methylphenoxy)acetate KCHSC = Kochia scoparia (kochia) TRZAW = Triticum aestivum (winter wheat)

Example 3—Greenhouse Trials

Following the protocol in Example 1, compound 1 and compound 2 were combined with 2,4 D EHE (EC) and applied to kochia (KCHSC, Kochia scoparia) and the phytotoxicity of the herbicidal compositions was measured. The condition of the test plants as compared with that of the control plants was determined visually and scored on a scale of 0 to 100 percent where 0 corresponds to no injury and 100 corresponds to complete kill. Colby's equation was used to determine the herbicidal effects expected from the mixtures. The results are summarized in Tables 11-12.

TABLE 11 Effect (% visual injury) of compound 1 and 2,4-D EHE on cereal weeds. Application rate (g ae/ha) compound 1 8.75 0 8.75 2,4-D EHE 0 280 280 KCHSC Obs 43 10 75 Exp — — 48 Δ 27 g ae/ha = grams acid equivalent per hectare 2,4-D EHE = 2-ethylhexyl (2,4-dichlorophenoxy)acetate KCHSC = Kochia scoparia (kochia)

TABLE 12 Effect (% visual injury) of compound 2 and 2,4-D EHE on cereal weeds. Application rate (g ae/ha) compound 2 8.75 0 8.75 2,4-D EHE 0 280 280 KCHSC Obs 55 10 68 Exp — — 60 Δ 8 g ae/ha = grams acid equivalent per hectare 2,4-D EHE = 2-ethylhexyl (2,4-dichlorophenoxy)acetate KCHSC = Kochia scoparia (kochia)

Example 4—Field Trials

Small plot field trials were established in Canada to evaluate efficacy and crop safety of Compound 7 with 2,4-D EHE. Trials were established as randomized complete blocks with 3-4 replicates. Individual plots were 2-3 meters (m) wide and 8-10 m long. Applications were made with backpack or tractor-mounted sprayers delivering a spray volume output of 100 liters per hectare (L/ha) using pressurized carbon dioxide (CO₂) as a propellant. Compound 7 was combined with 2,4 D EHE (660 g ae/L EC formulation) and applied to spring wheat (TRZAS), and the phytotoxicity of the herbicidal compositions was measured. In addition, the efficacy of the herbicidal composition on Canadian thistle (CIRAR, Cirsium arvense), kochia (KCHSC, Kochia scoparia), mallow (MALPU, Malva pusilla), wild buckwheat (POLCO, Polygonum convolvulus), and lady's thumb (POLPE, Polygonum persicaria) was evaluated. The condition of the test plants as compared with that of the control plants was determined visually and scored on a scale of 0 to 100 percent where 0 corresponds to no injury and 100 corresponds to complete kill. Colby's equation was used to determine the herbicidal effects expected from the mixtures. The results are summarized in Table 13.

TABLE 13 Effect (% visual injury) of compound 7 and 2,4-D EHE on cereal weeds. Application rate (g ae/ha) compound 7 35 0 35 2,4-D EHE 0 560 560 KCHSC 46-64 DAA Obs 62 25 81 Exp — — 72 Δ 10 POLCO 15 DAA Obs 50 51 84 Exp — — 76 Δ 9 POLPE 14-16 DAA Obs 20 55 71 Exp — — 64 Δ 7 CIRAR 46-64 DAA Obs 20 65 80 Exp — — 72 Δ 8 MALPU 26-33 DAA Obs 15 74 90 Exp — — 78 Δ 12 TRZAS 6-8 DAA Obs  3  3 5 Exp — — 6 Δ −1 TRZAS 14-16 DAA Obs  3  0 3 Exp — — 3 Δ 0 g ae/ha = grams acid equivalent per hectare DAA = days after exposure 2,4-D EHE = 2-ethylhexyl (2,4-dichlorophenoxy)acetate KCHSC = Kochia scoparia (kochia) POLCO = Polygonum convolvulus (wild buckwheat) POLPE = Polygonum persicaria (lady's thumb) CIRAR = Cirsium arvense (Canadian thistle) MALPU = Malva pusilla (mallow) TRZAS = Triticum aestivum (spring wheat)

Example 5—Greenhouse Trials

Following the protocol in Example 1, the herbicide 2,4 D EHE (EC) was combined with compound 1, compound 8, compound 9, compound 10, compound 11, compound 12, compound 13, compound 14, compound 15, and compound 16 and applied to winter wheat (TRZAW) and maize (ZEAMX), and the phytotoxicity of the herbicidal compositions was measured. In addition, the efficacy of the herbicidal compositions on velvetleaf (Abutilon theophrasti, ABUTH), pigweed (AMARE, Amaranthus retroflexus), spring rape (Brassica napus, BRSNN), common lambsquarters (Chenopodium album L., CHEAL), Canadian thistle (Cirsium arvense, CIRAR), nutsedge (Cyperus esculentus, CYPES), poinsettia (Euphorbia heterophylla, EPHHL), sunflower (Helianthus annus, HELAN), wild buckwheat (Polygonum convolvulus, POLCO), grain sorghum (Sorghum vulgare, SORVU), common chickweed (Stellaria media, STEME), and wild pansy (Viola tricolor, VIOTR) was evaluated. The condition of the test plants as compared with that of the control plants was determined visually and scored on a scale of 0 to 100 percent where 0 corresponds to no injury and 100 corresponds to complete kill. Colby's equation was used to determine the herbicidal effects expected from the mixtures. The results are summarized in Tables 14-23.

TABLE 14 Effect (% visual injury) of compound 1 and 2,4-D EHE on weeds. Application rate (g ae/ha) compound 1 5 0 5 2,4-D EHE 0 140 140 VIOTR Obs 25 35 70 Exp — — 51 Δ 19 CIRAR Obs 20 50 78 Exp — — 60 Δ 18 BRSNN Obs 60 60 96 Exp — — 84 Δ 12 SORVU Obs 13  0 35 Exp — — 13 Δ 23 CYPES Obs 25  0 70 Exp — — 25 Δ 45 g ae/ha = grams acid equivalent per hectare 2,4-D EHE = 2-ethylhexyl (2,4-dichlorophenoxy)acetate VIOTR = Viola tricolor (wild pansy) CIRAR = Cirsium arvense (Canadian thistle) BRSNN = Brassica napus (spring rape) SORVU = Sorghum vulgare (grain sorghum) CYPES = Cyperus esculentus (nutsedge)

TABLE 15 Effect (% visual injury) of compound 8 and 2,4-D EHE on weeds. Application rate (g ae/ha) compound 8 5 0 5 2,4-D EHE 0 140 140 VIOTR Obs 10 35 63 Exp — — 42 Δ 21 CIRAR Obs 30 50 80 Exp — — 65 Δ 15 BRSNN Obs 63 60 93 Exp — — 85 Δ 8 EPHHL Obs 84 35 100 Exp — — 90 Δ 10 ABUTH Obs 20 55 70 Exp — — 66 Δ 4 AMARE Obs 78 95 100 Exp — — 99 Δ 1 STEME Obs 45 63 80 Exp — — 79 Δ 1 TRZAW Obs  5  0 5 Exp — — 5 Δ 0 g ae/ha = grams acid equivalent per hectare 2,4-D EHE = 2-ethylhexyl (2,4-dichlorophenoxy)acetate VIOTR = Viola tricolor (wild pansy) CIRAR = Cirsium arvense (Canadian thistle) BRSNN = Brassica napus (spring rape) EPHHL = Euphorbia heterophylla (poinsettia) ABUTH = Abutilon theophrasti (velvetleaf) AMARE = Amaranthus retroflexus (pigweed) STEME = Stellaria media (common chickweed) TRZAW = Triticum aestivum (winter wheat)

TABLE 16 Effect (% visual injury) of compound 9 and 2,4-D EHE on weeds. Application rate (g ae/ha) compound 9 5 0 5 2,4-D EHE 0 140 140 VIOTR Obs 15 35 70 Exp — — 45 Δ 25 CIRAR Obs 10 50 75 Exp — — 55 Δ 20 BRSNN Obs 10 60 80 Exp — — 64 Δ 16 EPHHL Obs 60 35 83 Exp — — 74 Δ 9 CYPES Obs  0  0 40 Exp — — 0 Δ 40 POLCO Obs 25 55 70 Exp — — 66 Δ 4 TRZAW Obs  0  0 5 Exp — — 0 Δ 5 ZEAMX Obs  0  0 5 Exp — — 0 Δ 5 g ae/ha = grams acid equivalent per hectare 2,4-D EHE = 2-ethylhexyl (2,4-dichlorophenoxy)acetate VIOTR = Viola tricolor (wild pansy) CIRAR = Cirsium arvense (Canadian thistle) BRSNN = Brassica napus (spring rape) EPHHL = Euphorbia heterophylla (poinsettia) CYPES = Cyperus esculentus (nutsedge) POLCO = Polygonum convolvulus (wild buckwheat) TRZAW = Triticum aestivum (winter wheat) ZEAMX = Zea mays (maize)

TABLE 17 Effect (% visual injury) of compound 10 and 2,4-D EHE on weeds. Application rate (g ae/ha) compound 10 5 0 5 2,4-D EHE 0 140 140 VIOTR Obs 25 35 60 Exp — — 51 Δ 9 CIRAR Obs 15 50 84 Exp — — 58 Δ 27 BRSNN Obs 15 60 96 Exp — — 66 Δ 30 SORVU Obs  5  0 10 Exp — — 5 Δ 5 EPHHL Obs 75 35 93 Exp — — 84 Δ 9 CYPES Obs  5  0 10 Exp — — 5 Δ 5 ABUTH Obs 15 55 84 Exp — — 62 Δ 22 POLCO Obs 10 55 88 Exp — — 60 Δ 28 STEME Obs 70 63 88 Exp — — 89 Δ −1 TRZAW Obs  5  0 0 Exp — — 5 Δ −5 g ae/ha = grams acid equivalent per hectare 2,4-D EHE = 2-ethylhexyl (2,4-dichlorophenoxy)acetate VIOTR = Viola tricolor (wild pansy) CIRAR = Cirsium arvense (Canadian thistle) BRSNN = Brassica napus (spring rape) SORVU = Sorghum vulgare (grain sorghum) EPHHL = Euphorbia heterophylla (poinsettia) CYPES = Cyperus esculentus (nutsedge) ABUTH = Abutilon theophrasti (velvetleaf) POLCO = Polygonum convolvulus (wild buckwheat) STEME = Stellaria media (common chickweed) TRZAW = Triticum aestivum (winter wheat)

TABLE 18 Effect (% visual injury) of compound 11 and 2,4-D EHE on weeds. Application rate (g ae/ha) compound 11 5 0 5 2,4-D EHE 0 140 140 VIOTR Obs 10 35 70 Exp — — 42 Δ 29 STEME Obs 40 63 85 Exp — — 78 Δ 8 CIRAR Obs  5 50 80 Exp — — 53 Δ 28 BRSNN Obs 10 60 93 Exp — — 64 Δ 29 SORVU Obs  5  0 30 Exp — — 5 Δ 25 EPHHL Obs 25 35 65 Exp — — 51 Δ 15 CYPES Obs  0  0 15 Exp — — 0 Δ 15 POLCO Obs 10 55 100 Exp — — 60 Δ 41 TRZAW Obs 10  0 0 Exp — — 10 Δ −10 g ae/ha = grams acid equivalent per hectare 2,4-D EHE = 2-ethylhexyl (2,4-dichlorophenoxy)acetate VIOTR = Viola tricolor (wild pansy) STEME = Stellaria media (common chickweed) CIRAR = Cirsium arvense (Canadian thistle) BRSNN = Brassica napus (spring rape) SORVU = Sorghum vulgare (grain sorghum) EPHHL = Euphorbia heterophylla (poinsettia) CYPES = Cyperus esculentus (nutsedge) POLCO = Polygonum convolvulus (wild buckwheat) TRZAW = Triticum aestivum (winter wheat)

TABLE 19 Effect (% visual injury) of compound 12 and 2,4-D EHE on weeds. Application rate (g ae/ha) compound 12 5 0 5 2,4-D EHE 0 140 140 VIOTR Obs 18 35 68 Exp — — 46 Δ 21 CIRAR Obs 10 50 80 Exp — — 55 Δ 25 BRSNN Obs 50 60 95 Exp — — 80 Δ 15 EPHHL Obs 35 35 80 Exp — — 58 Δ 22 CYPES Obs  5  0 68 Exp — — 5 Δ 63 ABUTH Obs 10 55 90 Exp — — 60 Δ 31 CHEAL Obs 84 73 96 Exp — — 95 Δ 1 SORVU Obs  0  0 10 Exp — — 0 Δ 10 TRZAW Obs  0  0 5 Exp — — 0 Δ 5 ZEAMX Obs  0  0 0 Exp — — 0 Δ 0 g ae/ha = grams acid equivalent per hectare 2,4-D EHE = 2-ethylhexyl (2,4-dichlorophenoxy)acetate VIOTR = Viola tricolor (wild pansy) CIRAR = Cirsium arvense (Canadian thistle) BRSNN = Brassica napus (spring rape) EPHHL = Euphorbia heterophylla (poinsettia) CYPES = Cyperus esculentus (nutsedge) ABUTH = Abutilon theophrasti (velvetleaf) CHEAL = Chenopodium album L. (common lambsquarters) SORVU = Sorghum vulgare (grain sorghum) TRZAW = Triticum aestivum (winter wheat) ZEAMX = Zea mays (maize)

TABLE 20 Effect (% visual injury) of compound 13 and 2,4-D EHE on weeds. Application rate (g ae/ha) compound 13 5 0 5 2,4-D EHE 0 140 140 VIOTR Obs 25 35 78 Exp — — 51 Δ 26 CHEAL Obs 60 73 96 Exp — — 89 Δ 7 STEME Obs 50 63 85 Exp — — 81 Δ 4 CIRAR Obs 10 50 85 Exp — — 55 Δ 30 EPHHL Obs 75 35 100 Exp — — 84 Δ 16 CYPES Obs  0  0 40 Exp — — 0 Δ 40 ABUTH Obs  0 55 85 Exp — — 55 Δ 30 POLCO Obs 25 55 73 Exp — — 66 Δ 6 g ae/ha = grams acid equivalent per hectare 2,4-D EHE = 2-ethylhexyl (2,4-dichlorophenoxy)acetate VIOTR = Viola tricolor (wild pansy) CHEAL = Chenopodium album L. (common lambsquarters) STEME = Stellaria media (common chickweed) CIRAR = Cirsium arvense (Canadian thistle) EPHHL = Euphorbia heterophylla (poinsettia) CYPES = Cyperus esculentus (nutsedge) ABUTH = Abutilon theophrasti (velvetleaf) POLCO = Polygonum convolvulus (wild buckwheat)

TABLE 21 Effect (% visual injury) of compound 14 and 2,4-D EHE on weeds. Application rate (g ae/ha) compound 14 5 0 5 2,4-D EHE 0 140 140 VIOTR Obs 10 35 80 Exp — — 42 Δ 39 CHEAL Obs 15 73 83 Exp — — 77 Δ 6 CIRAR Obs  5 50 87 Exp — — 53 Δ 34 BRSNN Obs 10 60 88 Exp — — 64 Δ 24 HELAN Obs 10 75 87 Exp — — 78 Δ 9 EPHHL Obs 20 35 83 Exp — — 48 Δ 35 ABUTH Obs  0 55 68 Exp — — 55 Δ 13 SORVU Obs  0  0 5 Exp — — 0 Δ 5 TRZAW Obs  0  0 0 Exp — — 0 Δ 0 ZEAMX Obs  0  0 0 Exp — — 0 Δ 0 g ae/ha = grams acid equivalent per hectare 2,4-D EHE = 2-ethylhexyl (2,4-dichlorophenoxy)acetate VIOTR = Viola tricolor (wild pansy) CHEAL = Chenopodium album L. (common lambsquarters) CIRAR = Cirsium arvense (Canadian thistle) BRSNN = Brassica napus (spring rape) HELAN = Helianthus annus (sunflower) EPHHL = Euphorbia heterophylla (poinsettia) ABUTH = Abutilon theophrasti (velvetleaf) SORVU = Sorghum vulgare (grain sorghum) TRZAW = Triticum aestivum (winter wheat) ZEAMX = Zea mays (maize)

TABLE 22 Effect (% visual injury) of compound 15 and 2,4-D EHE on weeds. Application rate (g ae/ha) compound 15 5 0 5 2,4-D EHE 0 140 140 VIOTR Obs 33 35 73 Exp — — 56 Δ 16 CIRAR Obs 15 50 83 Exp — — 58 Δ 25 SORVU Obs  0  0 10 Exp — — 0 Δ 10 EPHHL Obs 73 35 90 Exp — — 82 Δ 8 CYPES Obs 25  0 30 Exp — — 25 Δ 5 ABUTH Obs 30 55 85 Exp — — 69 Δ 17 POLCO Obs 30 55 100 Exp — — 69 Δ 32 HELAN Obs 90 75 100 Exp — — 98 Δ 3 TRZAW Obs  5  0 5 Exp — — 5 Δ 0 ZEAMX Obs  0  0 0 Exp — — 0 Δ 0 g ae/ha = grams acid equivalent per hectare 2,4-D EHE = 2-ethylhexyl (2,4-dichlorophenoxy)acetate VIOTR = Viola tricolor (wild pansy) CIRAR = Cirsium arvense (Canadian thistle) SORVU = Sorghum vulgare (grain sorghum) EPHHL = Euphorbia heterophylla (poinsettia) CYPES = Cyperus esculentus (nutsedge) ABUTH = Abutilon theophrasti (velvetleaf) POLCO = Polygonum convolvulus (wild buckwheat) HELAN = Helianthus annus (common sunflower) TRZAW = Triticum aestivum (winter wheat) ZEAMX = Zea mays (maize)

TABLE 23 Effect (% visual injury) of compound 16 and 2,4-D EHE on weeds. Application rate (g ae/ha) compound 16 5 0 5 2,4-D EHE 0 140 140 10284BRSNN Obs 60 60 96 Exp 84 Δ 12 CIRAR Obs 20 50 78 Exp 60 Δ 18 CYPES Obs 25 0 70 Exp 25 Δ 45 SORVU Obs 13 0 35 Exp 13 Δ 23 VIOTR Obs 25 35 70 Exp 51 Δ 19 TRZAW Obs 0 0 0 Exp 0 Δ 0 g ae/ha = grams acid equivalent per hectare 2,4-D EHE = 2-ethylhexyl (2,4-dichlorophenoxy)acetate BRSNN = Brassica napus (spring rape) CIRAR = Cirsium arvense (Canadian thistle) CYPES = Cyperus esculentus (nutsedge) SORVU = Sorghum vulgare (grain sorghum) VIOTR = Viola tricolor (wild pansy) TRZAW = Triticum aestivum (winter wheat)

Example 6—Greenhouse Trials

Following the protocol in Example 1, compound 1 (SC) was combined with 2,4 D EHE (EC), Arylex™ (halauxifen-methyl; SC), fluroxypyr-MHE (EC), and MCPA EHE, and Compound 2 (SC) was combined with 2,4 D EHE (EC) and Arylex™ (halauxifen-methyl, SC). The mixtures were applied to spring barley (HORVS) and winter wheat (TRZAW), and the phytotoxicity of the herbicidal compositions was measured. In addition, the efficacy of the herbicidal composition on pigweed (Amaranthus retroflexus, AMARE), black mustard (Brassica nigra, BRSNI), winter rape (Brassica napus, BRSNW), turnip (Brassica rapa, BRSRR), kochia (Kochia scoparia, KCHSC), wild buckwheat (Polygonum convolvulus, POLCO), wild radish (Raphanus raphanistrum, RAPRA), Russian thistle (Salsola iberica, SASKR), wild mustard (Sinapis arvensis, SINAR), Indian hedge mustard (Sisymbrium orientale, SSYOR), and wild pansy (Viola tricolor, VIOTR) was evaluated. The condition of the test plants as compared with that of the control plants was determined visually and scored on a scale of 0 to 100 percent where 0 corresponds to no injury and 100 corresponds to complete kill. Colby's equation was used to determine the herbicidal effects expected from the mixtures. The results are summarized in Tables 24-30.

TABLE 24 Effect (% visual injury) of compound 1 (SC) and 2,4-D EHE on weeds. Application compound 1 SC (g ae/ha) 5 10 0 5 10 Rate 2,4-D EHE (g ae/ha) 0 0 420 420 420 POLCO Obs 30 30 60 80 80 Exp 72 72 Δ 8 8 HORVS Obs 0 0 0 0 0 Exp 0 0 Δ 0 0 TRZAW Obs 0 0 0 5 5 Exp 0 0 Δ 5 5 g ae/ha = grams acid equivalent per hectare POLCO = Polygonum convolvulus (wild buckwheat) HORVS = (Hordeum vulgare, barley) TRZAW = Triticum aestivum (winter wheat)

TABLE 25 Effect (% visual injury) of compound 1 (SC) and 2,4-D EHE on weeds. Application compound 1 SC (g ae/ha) 5 10 0 5 10 Rate 2,4-D EHE (g ae/ha) 0 0 400 400 400 BRSNW Obs 30 60 93 100 100 Exp 95 93 Δ 5 7 POLCO Obs 10 40 80 100 100 Exp 82 80 Δ 18 20 SINAR Obs 100 80 97 100 100 Exp 100 97 Δ 0 3 TRZAW Obs 20 15 10 20 25 Exp 28 22 Δ −8 3 g ae/ha = grams acid equivalent per hectare BRSNW = Brassica napus (winter rape) POLCO = Polygonum convolvulus (wild buckwheat) SINAR = Sinapis arvensis (wild mustard) TRZAW = Triticum aestivum (winter wheat)

TABLE 26 Effect (% visual injury) of compound 2 (SC) and 2,4-D EHE on weeds. Application compound 2 SC (g ae/ha) 5 10 0 5 10 Rate 2,4-D EHE (g ae/ha) 0 0 400 400 400 BRSNW Obs 50 50 93 100 100 Exp 97 93 Δ 4 7 POLCO Obs 30 50 80 100 100 Exp 86 80 Δ 14 20 SINAR Obs 100 100 97 100 100 Exp 100 97 Δ 0 3 TRZAW Obs 10 20 10 15 15 Exp 19 27 Δ −4 −12 g ae/ha = grams acid equivalent per hectare BRSNW = Brassica napus (winter rape) POLCO = Polygonum convolvulus (wild buckwheat) SINAR = Sinapis arvensis (wild mustard) TRZAW = Triticum aestivum (winter wheat)

TABLE 27 Effect (% visual injury) of compound 1 (SC) and Arylex ™ (halauxifen-methyl) on weeds. Application compound 1 SC (g ae/ha) 2.5 5 0 0 2.5 5 Rate Arylex ™ (g ae/ha) 0 0 2.5 5 2.5 5 BRSRR Obs 45 62 10 13 62 68 Exp 51 67 Δ 11 2 RAPRA Obs 13 13 10 20 37 47 Exp 22 31 Δ 15 16 SSYOR Obs 13 20 57 63 70 73 Exp 62 71 Δ 8 3 VIOTR Obs 13 23 15 20 30 40 Exp 26 39 Δ 4 1 g ae/ha = grams acid equivalent per hectare BRSRR = Brassica rapa (turnip) RAPRA = Raphanus raphanistrum (wild radish) SSYOR = Sisymbrium orientale (Indian hedge mustard) VIOTR = Viola tricolor (wild pansy)

TABLE 28 Effect (% visual injury) of compound 2 (SC) and Arylex ™ (halauxifen-methyl) on weeds. Application compound 2 SC (g ae/ha) 2.5 5 0 0 2.5 5 Rate Arylex ™ (g ae/ha) 0 0 2.5 5 2.5 5 BRSNI Obs 30 70 0 0 43 65 Exp 30 70 Δ 13 −5 BRSRR Obs 23 67 10 13 57 73 Exp 31 71 Δ 26 1 RAPRA Obs 17 25 10 20 53 50 Exp 25 40 Δ 28 10 SINAR Obs 87 94 65 78 98 96 Exp 95 99 Δ 2 −3 SSYOR Obs 20 40 57 63 70 85 Exp 65 78 Δ 5 7 VIOTR Obs 13 23 15 20 40 45 Exp 26 39 Δ 14 6 g ae/ha = grams acid equivalent per hectare BRSNI = Brassica nigra (black mustard) BRSRR = Brassica rapa (turnip) RAPRA = Raphanus raphanistrum (wild radish) SINAR = Sinapis arvensis (wild mustard) SSYOR = Sisymbrium orientale (Indian hedge mustard) VIOTR = Viola tricolor (wild pansy)

TABLE 29 Effect (% visual injury) of compound 1 (SC) and fluroxypyr-MHE on weeds. Application compound 1 SC (g ae/ha) 5 10 0 5 10 Rate fluroxypyr-MHE (g ae/ha) 0 0 70 70 70 AMARE Obs 70 85 50 100 100 Exp 85 93 Δ 15 8 KCHSC Obs 75 100 93 100 100 Exp 98 100 Δ 2 0 POLCO Obs 30 30 75 100 100 Exp 83 83 Δ 18 18 SASKR Obs 65 80 95 100 100 Exp 98 99 Δ 2 1 HORVS Obs 0 0 0 0 0 Exp 0 0 Δ 0 0 TRZAW Obs 0 0 0 0 0 Exp 0 0 Δ 0 0 g ae/ha = grams acid equivalent per hectare AMARE = Amaranthus retroflexus (pigweed) KCHSC = Kochia scoparia (kochia) POLCO = Polygonum convolvulus (wild buckwheat) SASKR = Salsola iberica (Russian thistle) HORVS = Hordeum vulgare (barley) TRZAW = Triticum aestivum (winter wheat)

TABLE 30 Effect (% visual injury) of compound 1 (SC) and MCPA EHE on weeds. Application compound 1 5 10 0 5 10 Rate SC (g ae/ha) MCPA 0 0 420 420 420 EHE (g ae/ha) POLCO Obs 30 30 65 80 100 Exp 76 76 Δ 5 25 HORVS Obs 0 0 0 0 10 Exp 0 0 Δ 0 10 TRZAW Obs 0 0 0 0 0 Exp 0 0 Δ 0 0 g ae/ha = grams acid equivalent per hectare POLCO = Polygonum convolvulus (wild buckwheat) HORVS = Hordeum vulgare (barley) TRZAW = Triticum aestivum (winter wheat)

Example 7—Greenhouse Trials

Following the protocol in Example 1, compound 1 (EC) was combined with 2,4-D EHE (EC), 2,4-D DMA (as Weedar™ 64), 2,4-D choline, 2,4-DB DMA (as Butyrac 200), aminocyclopyrachlor (SL), aminopyralid-triisopropanolammonium (TIPA, as Milestone™, SL), Arylex™ (halauxifen-methyl, SC), clopyralid (as Lontrel™ 35A Herbicidal Concentrate), dicamba-dimethylammonium salt (as Banvel® 4S), dichlorprop-P (as the potassium salt), fluroxypyr-MHE (EC), MCPA EHE, MCPA DMA, mecoprop-P (as the potassium salt), picloram-potassium (as Tordon™ 22K), Rinskor™ (as the benzyl ester, SC), quinclorac (as Facet® 75 DF), and triclopyr-butotyl (as Garlon 4 Ultra), and Compound 2 (EC) was combined with 2,4 D EHE (EC), aminopyralid-triisopropanolammonium (TIPA, as Milestone™, SL), clopyralid (as Lontrel™ 35A Herbicidal Concentrate), dicamba-dimethylammonium salt (as Banvel® 4S), fluroxypyr-MHE (EC) and MCPA EHE. The mixtures were applied to spring barley (HORVS), maize (ZEAMX), common rice (ORYSA) and winter wheat (TRZAW), and the phytotoxicity of the herbicidal compositions was measured. In addition, the efficacy of the herbicidal composition on velvetleaf (Abutilon theophrasti, ABUTH), blackgrass (Alopecurus myosuroides, ALOMY), pigweed (Amaranthus retroflexus, AMARE), wild oat (Avenafatua, AVEFA), Chinese kale (Brassica alboglabra, BRSAG), brown mustard (Brassica juncea, BRSJU), rutabaga (Brassica napus var. napobrassica, BRSNA), spring rape (Brassica napus, BRSNN), winter rape (Brassica napus, BRSNW), common lambsquarters (Chenopodium album L., CHEAL), Canadian thistle (Cirsium arvense, CIRAR), nutsedge (Cyperus esculentus, CYPES), large crabgrass (Digitaria sanguinalis, DIGSA), bamyardgrass (Echinochloa crus-galli, ECHCG), poinsettia (Euphorbia heterophylla, EPHHL), soybean (Glycine max, GLXMA), common sunflower (Helianthus annuus, HELAN), ivyleaf morningglory (Ipomoea hederacea, IPOHE), kochia (Kochia scoparia, KCHSC), wild buckwheat (Polygonum convolvulus, POLCO), Russian thistle (Salsola iberica, SASKR), wild mustard (Sinapis arvensis, SINAR), grain sorghum (Sorghum vulgare, SORVU), common chickweed (Stellaria media, STEME), ivyleaved speedwell (Veronica hederifolia, VERHE), wild pansy (Viola tricolor, VIOTR) was evaluated. The condition of the test plants as compared with that of the control plants was determined visually and scored on a scale of 0 to 100 percent where 0 corresponds to no injury and 100 corresponds to complete kill. Colby's equation was used to determine the herbicidal effects expected from the mixtures. The results are summarized in Tables 31-59.

TABLE 31 Effect (% visual injury) of compound 1 (EC) and 2,4-D EHE on weeds. Application compound 1 5 10 0 5 10 Rate (g ae/ha) 2,4-D EHE 0 0 420 420 420 (g ae/ha) POLCO Obs 30 30 60 70 100 Exp 72 72 Δ −2 28 HORVS Obs 0 0 0 0 0 Exp 0 0 Δ 0 0 TRZAW Obs 0 0 0 0 5 Exp 0 0 Δ 0 5 g ae/ha = grams acid equivalent per hectare HORVS = Hordeum vulgare (barley) POLCO = Polygonum convolvulus (wild buckwheat) TRZAW = Triticum aestivum (winter wheat)

TABLE 32 Effect (% visual injury) of compound 1 (EC) and 2,4-D EHE on weeds. Application compound 1 5 10 0 5 10 Rate (g ae/ha) 2,4-D EHE 0 0 400 400 400 (g ae/ha) BRSNW Obs 40 100 93 100 100 Exp 96 93 Δ 4 7 POLCO Obs 100 80 80 100 100 Exp 100 80 Δ 0 20 SASKR Obs 10 65 70 90 93 Exp 73 77 Δ 17 17 SINAR Obs 100 100 97 100 100 Exp 100 97 Δ 0 3 HORVS Obs 0 0 10 0 0 Exp 10 10 Δ −10 −10 TRZAW Obs 0 0 10 0 10 Exp 10 10 Δ −10 0 g ae/ha = grams acid equivalent per hectare BRSNW = Brassica napus (winter rape) HORVS = Hordeum vulgare (barley) POLCO = Polygonum convolvulus (wild buckwheat) SASKR = Salsola iberica (Russian thistle) SINAR = Sinapis arvensis (wild mustard) TRZAW = Triticum aestivum (winter wheat)

TABLE 33 Effect (% visual injury) of compound 1 (EC) and 2,4-D EHE on weeds. Application Rate compound 1 (g ae/ha) 5 0 5 2,4-D EHE (g ae/ha) 0 400 400 BRSNN Obs 50 75 100 Exp 88 Δ 13 CIRAR Obs 10 70 75 Exp 73 Δ 2 EPHHL Obs 95 60 100 Exp 98 Δ 2 KCHSC Obs 65 10 75 Exp 69 Δ 7 STEME Obs 60 10 65 Exp 64 Δ 1 VIOTR Obs 10 65 70 Exp 69 Δ 2 ORYSA Obs 0 0 0 Exp 0 Δ 0 TRZAW Obs 10 0 5 Exp 10 Δ −5 ZEAMX Obs 5 0 0 Exp 5 Δ −5 g ae/ha = grams acid equivalent per hectare BRSNN = Brassica napus (spring rape) CIRAR = Cirsium arvense (Canadian thistle) EPHHL = Euphorbia heterophylla (poinsettia) KCHSC = Kochia scoparia (kochia) VIOTR = Viola tricolor (wild pansy) ORYSA = Oryza sativa (common rice) STEME = Stellaria media (common chickweed) TRZAW = Triticum aestivum (winter wheat) ZEAMX = Zea mays (maize)

TABLE 34 Effect (% visual injury) of compound 1 (EC) and 2,4-D choline on weeds. Application Rate compound 1 (g ae/ha) 5 0 5 2,4-D choline (g ae/ha) 0 400 400 BRSAG Obs 15 85 93 Exp 87 Δ 6 BRSJU Obs 60 90 97 Exp 96 Δ 1 BRSNA Obs 65 93 99 Exp 98 Δ 1 g ae/ha = grams acid equivalent per hectare BRSAG = Brassica alboglabra (Chinese kale) BRSJU = Brassica juncea (brown mustard) BRSNA = Brassica napus var. napobrassica (rutabaga)

TABLE 35 Effect (% visual injury) of compound 1 (EC) and 2,4-D DMA on weeds. Application Rate compound 1 (g ae/ha) 5 0 5 2,4-DMA (g ae/ha) 0 400 400 ABUTH Obs 70 75 97 Exp 93 Δ 5 BRSNN Obs 50 85 100 Exp 93 Δ 8 CIRAR Obs 10 70 85 Exp 73 Δ 12 CYPES Obs 30 30 60 Exp 51 Δ 9 HELAN Obs 80 80 100 Exp 96 Δ 4 IPOHE Obs 20 80 100 Exp 84 Δ 16 KCHSC Obs 65 10 75 Exp 69 Δ 7 VIOTR Obs 10 65 80 Exp 69 Δ 12 ORYSA Obs 0 0 0 Exp 0 Δ 0 TRZAW Obs 10 0 0 Exp 10 Δ −10 ZEAMX Obs 5 0 0 Exp 5 Δ −5 g ae/ha = grams acid equivalent per hectare ABUTH = Abutilon theophrasti (velvetleaf) BRSNN = Brassica napus (spring rape) CIRAR = Cirsium arvense (Canadian thistle) CYPES = Cyperus esculentus (nutsedge) HELAN = Helianthus annuus (sunflower) IPOHE = Ipomoea hederacea (ivyleaf morningglory) KCHSC = Kochia scoparia (kochia) ORYSA = Oryza sativa (common rice) TRZAW = Triticum aestivum (winter wheat) VIOTR = Viola tricolor (wild pansy) ZEAMX = Zea mays (maize)

TABLE 36 Effect (% visual injury) of compound 1 (EC) and 2,4-DB DMA on weeds. Application Rate compound 1 (g ae/ha) 5 0 5 2,4-DB DMA (g ae/ha) 0 400 400 BRSNN Obs 50 70 100 Exp 85 Δ 15 CIRAR Obs 10 40 70 Exp 46 Δ 24 CYPES Obs 30 0 50 Exp 30 Δ 20 EPHHL Obs 95 10 100 Exp 96 Δ 5 IPOHE Obs 20 70 85 Exp 76 Δ 9 KCHSC Obs 65 10 80 Exp 69 Δ 12 POLCO Obs 95 60 100 Exp 98 Δ 2 ORYSA Obs 0 0 0 Exp 0 Δ 0 TRZAW Obs 10 10 15 Exp 19 Δ −4 ZEAMX Obs 5 0 0 Exp 5 Δ −5 g ae/ha = grams acid equivalent per hectare BRSNN = Brassica napus (spring rape) CIRAR = Cirsium arvense (Canadian thistle) CYPES = Cyperus esculentus (nutsedge) EPHHL = Euphorbia heterophylla (poinsettia) IPOHE = Ipomoea hederacea (ivyleaf morningglory) KCHSC = Kochia scoparia (kochia) ORYSA = Oryza sativa (common rice) POLCO = Polygonum convolvulus (wild buckwheat) TRZAW = Triticum aestivum (winter wheat) ZEAMX = Zea mays (maize)

TABLE 37 Effect (% visual injury) of compound 1 (EC) and aminocyclopyrachlor on weeds. Application Rate compound 1 (g ae/ha) 5 0 5 aminocyclopyrachlor (g ae/ha) 0 100 100 VERHE Obs 40 75 99 Exp 85 Δ 14 g ae/ha = grams acid equivalent per hectare VERHE = Veronica hederifolia (ivyleaved speedwell)

TABLE 38 Effect (% visual injury) of compound 1 (EC) and aminopyralid-TIPA on weeds. Application Rate compound 1 (g ae/ha) 5 0 5 aminopyralid-TIPA (g ae/ha) 0 5 5 BRSNN Obs 50 10 80 Exp 55 Δ 25 CIRAR Obs 10 60 75 Exp 64 Δ 11 HELAN Obs 80 60 97 Exp 92 Δ 5 IPOHE Obs 20 60 70 Exp 68 Δ 2 KCHSC Obs 65 10 75 Exp 69 Δ 7 POLCO Obs 95 65 100 Exp 98 Δ 2 SORVU Obs 30 0 70 Exp 30 Δ 40 STEME Obs 60 60 93 Exp 84 Δ 9 VIOTR Obs 10 10 30 Exp 19 Δ 11 ORYSA Obs 0 0 0 Exp 0 Δ 0 TRZAW Obs 10 0 10 Exp 10 Δ 0 ZEAMX Obs 5 0 0 Exp 5 Δ −5 g ae/ha = grams acid equivalent per hectare BRSNN = Brassica napus (spring rape) CIRAR = Cirsium arvense (Canadian thistle) HELAN = Helianthus annuus (sunflower) IPOHE = Ipomoea hederacea (ivyleaf morningglory) KCHSC = Kochia scoparia (kochia) ORYSA = Oryza sativa (common rice) POLCO = Polygonum convolvulus (wild buckwheat) SORVU = Sorghum vulgare (grain sorghum) STEME = Stellaria media (common chickweed) TRZAW = Triticum aestivum (winter wheat) VIOTR = Viola tricolor (wild pansy) ZEAMX = Zea mays (maize)

TABLE 39 Effect (% visual injury) of compound 1 (EC) and Arylex ™ on weeds. Application Rate compound 1 g ae/ha) 5 0 5 Arylex ™ (g ae/ha) 0 2.5 2.5 BRSNN Obs 50 20 85 Exp 60 Δ 25 CIRAR Obs 10 50 75 Exp 55 Δ 20 IPOHE Obs 20 10 50 Exp 28 Δ 22 SORVU Obs 30 0 70 Exp 30 Δ 40 ORYSA Obs 0 0 0 Exp 0 Δ 0 TRZAW Obs 10 0 0 Exp 10 Δ −10 ZEAMX Obs 5 0 10 Exp 5 Δ 5 g ae/ha = grams acid equivalent per hectare BRSNN = Brassica napus (spring rape) CIRAR = Cirsium arvense (Canadian thistle) IPOHE = Ipomoea hederacea (ivyleaf morningglory) ORYSA = Oryza sativa (common rice) SORVU = Sorghum vulgare (grain sorghum) TRZAW = Triticum aestivum (winter wheat) ZEAMX = Zea mays (maize)

TABLE 40 Effect (% visual injury) of compound 1 (EC) and clopyralid on weeds. Application Rate compound 1 (g ae/ha) 5 0 5 clopyralid (g ae/ha) 0 120 120 CHEAL Obs 80 10 85 Exp 82 Δ 3 IPOHE Obs 20 30 65 Exp 44 Δ 21 KCHSC Obs 65 10 75 Exp 69 Δ 7 STEME Obs 60 0 70 Exp 60 Δ 10 ORYSA Obs 0 0 0 Exp 0 Δ 0 TRZAW Obs 10 0 0 Exp 10 Δ −10 ZEAMX Obs 5 0 0 Exp 5 Δ −5 g ae/ha = grams acid equivalent per hectare CHEAL = Chenopodium album L. (common lambsquarters) IPOHE = Ipomoea hederacea (ivyleaf morningglory) KCHSC = Kochia scoparia (kochia) ORYSA = Oryza sativa (common rice) STEME = Stellaria media (common chickweed) TRZAW = Triticum aestivum (winter wheat) ZEAMX = Zea mays (maize)

TABLE 41 Effect (% visual injury) of compound 1 (EC) and dicamba-DMA on weeds. Application Rate compound 1 (g ae/ha) 5 0 5 dicamba-DMA (g ae/ha) 0 150 150 BRSNN Obs 50 40 85 Exp 70 Δ 15 CIRAR Obs 10 70 75 Exp 73 Δ 2 EPHHL Obs 95 50 100 Exp 98 Δ 3 IPOHE Obs 20 70 80 Exp 76 Δ 4 VIOTR Obs 10 20 40 Exp 28 Δ 12 ORYSA Obs 0 0 0 Exp 0 Δ 0 TRZAW Obs 10 0 0 Exp 10 Δ −10 ZEAMX Obs 5 0 5 Exp 5 Δ 0 g ae/ha = grams acid equivalent per hectare BRSNN = Brassica napus (spring rape) CIRAR = Cirsium arvense (Canadian thistle) EPHHL = Euphorbia heterophylla (poinsettia) IPOHE = Ipomoea hederacea (ivyleaf morningglory) ORYSA = Oryza sativa (common rice) TRZAW = Triticum aestivum (winter wheat) VIOTR = Viola tricolor (wild pansy) ZEAMX = Zea mays (maize)

TABLE 42 Effect (% visual injury) of compound 1 (EC) and dichlorprop-P on weeds. Application Rate compound 1 (g ae/ha) 5 0 5 dichlorprop-P (g ae/ha) 0 400 400 ABUTH Obs 70 60 100 Exp 88 Δ 12 BRSNN Obs 50 80 95 Exp 90 Δ 5 CIRAR Obs 10 70 80 Exp 73 Δ 7 CYPES Obs 30 0 65 Exp 30 Δ 35 EPHHL Obs 95 60 100 Exp 98 Δ 2 HELAN Obs 80 85 100 Exp 97 Δ 3 STEME Obs 60 20 90 Exp 68 Δ 22 ORYSA Obs 0 0 0 Exp 0 Δ 0 TRZAW Obs 10 0 0 Exp 10 Δ −10 g ae/ha = grams acid equivalent per hectare ABUTH = Abutilon theophrasti (velvetleaf) BRSNN = Brassica napus (spring rape) CIRAR = Cirsium arvense (Canadian thistle) CYPES = Cyperus esculentus (nutsedge) EPHHL = Euphorbia heterophylla (poinsettia) HELAN = Helianthus annuus (sunflower) ORYSA = Oryza sativa (common rice) STEME = Stellaria media (common chickweed) TRZAW = Triticum aestivum (winter wheat)

TABLE 43 Effect (% visual injury) of compound 1 (EC) and fluroxypyr-MHE on weeds. Application Rate compound 1 (g ae/ha) 5 0 5 fluroxypyr-MHE (g ae/ha) 0 100 100 ABUTH Obs 70 70 100 Exp 91 Δ 9 BRSNN Obs 50 85 97 Exp 93 Δ 5 CIRAR Obs 10 60 70 Exp 64 Δ 6 ECHCG Obs 65 0 70 Exp 65 Δ 5 HELAN Obs 80 80 100 Exp 96 Δ 4 KCHSC Obs 65 65 90 Exp 88 Δ 2 VIOTR Obs 10 80 93 Exp 82 Δ 11 ORYSA Obs 0 0 0 Exp 0 Δ 0 TRZAW Obs 10 0 0 Exp 10 Δ −10 ZEAMX Obs 5 0 10 Exp 5 Δ 5 g ae/ha = grams acid equivalent per hectare ABUTH = Abutilon theophrasti (velvetleaf) BRSNN = Brassica napus (spring rape) CIRAR = Cirsium arvense (Canadian thistle) ECHCG = Echinochloa crus-galli (barnyardgrass) HELAN = Helianthus annuus (sunflower) KCHSC = Kochia scoparia (kochia) ORYSA = Oryza sativa (common rice) TRZAW = Triticum aestivum (winter wheat) VIOTR = Viola tricolor (wild pansy) ZEAMX = Zea mays (maize)

TABLE 44 Effect (% visual injury) of compound 1 (EC) and fluroxypyr-MHE on weeds. Application compound 1 5 10 0 5 10 Rate (g ae/ha) fluroxypyr- 0 0 70 70 70 MHE (g ae/ha) AMARE Obs 70 85 50 100 97 Exp 85 93 Δ 15 5 BRSNW Obs 70 80 95 100 100 Exp 99 99 Δ 2 1 POLCO Obs 30 30 75 100 100 Exp 83 83 Δ 18 18 SASKR Obs 40 60 95 100 95 Exp 97 98 Δ 3 −3 SINAR Obs 95 100 85 100 100 Exp 99 100 Δ 1 0 HORVS Obs 0 0 0 5 0 Exp 0 0 Δ 5 0 TRZAW Obs 0 0 0 10 0 Exp 0 0 Δ 10 0 g ae/ha = grams acid equivalent per hectare AMARE = Amaranthus retroflexus (pigweed) BRSNW = Brassica napus (winter rape) HORVS = Hordeum vulgare (barley) POLCO = Polygonum convolvulus (wild buckwheat) SASKR = Salsola iberica, (Russian thistle) SINAR = Sinapis arvensis, (wild mustard) TRZAW = Triticum aestivum (winter wheat)

TABLE 45 Effect (% visual injury) of compound 1 (EC) and MCPA EHE on weeds. Application Rate compound 1 (g ae/ha) 5 0 5 MCPA EHE (g ae/ha) 0 280 280 ABUTH Obs 70 65 95 Exp 90 Δ 6 BRSNN Obs 50 95 100 Exp 98 Δ 3 CIRAR Obs 10 75 83 Exp 78 Δ 6 CYPES Obs 30 50 87 Exp 65 Δ 22 KCHSC Obs 65 0 85 Exp 65 Δ 20 POLCO Obs 95 70 100 Exp 99 Δ 2 STEME Obs 60 10 70 Exp 64 Δ 6 VIOTR Obs 10 75 93 Exp 78 Δ 16 ORYSA Obs 0 0 0 Exp 0 Δ 0 TRZAW Obs 10 0 0 Exp 10 Δ −10 ZEAMX Obs 5 0 0 Exp 5 Δ −5 g ae/ha = grams acid equivalent per hectare ABUTH = Abutilon theophrasti (velvetleaf) BRSNN = Brassica napus (spring rape) CIRAR = Cirsium arvense (Canadian thistle) CYPES = Cyperus esculentus (nutsedge) KCHSC = Kochia scoparia (kochia) ORYSA = Oryza sativa (common rice) POLCO = Polygonum convolvulus (wild buckwheat) STEME = Stellaria media (common chickweed) TRZAW = Triticum aestivum (winter wheat) VIOTR = Viola tricolor (wild pansy) ZEAMX = Zea mays (maize)

TABLE 46 Effect (% visual injury) of compound 1 (EC) and MCPA EHE on weeds. Application compound 1 5 10 0 5 10 Rate (g ae/ha) MCPA EHE 0 0 420 420 420 (g ae/ha) POLCO Obs 30 30 65 70 95 Exp 76 76 Δ −6 20 HORVS Obs 0 0 0 0 0 Exp 0 0 Δ 0 0 TRZAW Obs 0 0 0 0 0 Exp 0 0 Δ 0 0 g ae/ha = grams acid equivalent per hectare HORVS = Hordeum vulgare (barley) POLCO = Polygonum convolvulus (wild buckwheat) TRZAW = Triticum aestivum (winter wheat)

TABLE 47 Effect (% visual injury) of compound 1 (EC) and MCPA DMA on weeds. Application Rate compound 1 (g ae/ha) 5 0 5 MCPA DMA (g ae/ha) 0 400 400 BRSNN Obs 50 95 100 Exp 98 Δ 3 CIRAR Obs 10 65 70 Exp 69 Δ 2 STEME Obs 60 20 95 Exp 68 Δ 27 VIOTR Obs 10 30 50 Exp 37 Δ 13 ORYSA Obs 0 0 0 Exp 0 Δ 0 TRZAW Obs 10 0 0 Exp 10 Δ −10 g ae/ha = grams acid equivalent per hectare BRSNN = Brassica napus (spring rape) CIRAR = Cirsium arvense (Canadian thistle) STEME = Stellaria media (common chickweed) TRZAW = Triticum aestivum (winter wheat) VIOTR = Viola tricolor (wild pansy) ZEAMX = Zea mays (maize)

TABLE 48 Effect (% visual injury) of compound 1 (EC) and mecoprop-P on weeds. Application Rate compound 1 (g ae/ha) 5 0 5 mecoprop-P (g ae/ha) 0 400 400 ABUTH Obs 70 30 100 Exp 79 Δ 21 BRSNN Obs 50 30 80 Exp 65 Δ 15 CIRAR Obs 10 10 80 Exp 19 Δ 61 EPHHL Obs 95 30 100 Exp 97 Δ 4 IPOHE Obs 20 30 70 Exp 44 Δ 26 KCHSC Obs 65 10 80 Exp 69 Δ 12 SORVU Obs 30 0 60 Exp 30 Δ 30 STEME Obs 60 0 80 Exp 60 Δ 20 ORYSA Obs 0 0 0 Exp 0 Δ 0 TRZAW Obs 10 0 10 Exp 10 Δ 0 ZEAMX Obs 5 0 0 Exp 5 Δ −5 g ae/ha = grams acid equivalent per hectare ABUTH = Abutilon theophrasti (velvetleaf) BRSNN = Brassica napus (spring rape) CIRAR = Cirsium arvense (Canadian thistle) EPHHL = Euphorbia heterophylla (poinsettia) IPOHE = Ipomoea hederacea (ivyleaf morningglory) KCHSC = Kochia scoparia (kochia) ORYSA = Oryza sativa (common rice) SORVU = Sorghum vulgare (grain sorghum) STEME = Stellaria media (common chickweed) TRZAW = Triticum aestivum (winter wheat) ZEAMX = Zea mays (maize)

TABLE 49 Effect (% visual injury) of compound 1 (EC) and picloram-potassium on weeds. Application Rate compound 1 (g ae/ha) 5 0 5 picloram-potassium (g ae/ha) 0 10 10 ABUTH Obs 70 35 100 Exp 81 Δ 20 BRSNN Obs 50 20 80 Exp 60 Δ 20 CIRAR Obs 10 60 80 Exp 64 Δ 16 CYPES Obs 30 0 60 Exp 30 Δ 30 EPHHL Obs 95 20 100 Exp 96 Δ 4 IPOHE Obs 20 40 60 Exp 52 Δ 8 KCHSC Obs 65 0 85 Exp 65 Δ 20 SORVU Obs 30 0 60 Exp 30 Δ 30 VIOTR Obs 10 0 20 Exp 10 Δ 10 ORYSA Obs 0 0 0 Exp 0 Δ 0 TRZAW Obs 10 0 0 Exp 10 Δ −10 ZEAMX Obs 5 0 0 Exp 5 Δ −5 g ae/ha = grams acid equivalent per hectare ABUTH = Abutilon theophrasti (velvetleaf) BRSNN = Brassica napus (spring rape) CIRAR = Cirsium arvense (Canadian thistle) CYPES = Cyperus esculentus (nutsedge) EPHHL = Euphorbia heterophylla (poinsettia) IPOHE = Ipomoea hederacea (ivyleaf morningglory) KCHSC = Kochia scoparia (kochia) ORYSA = Oryza sativa (common rice) SORVU = Sorghum vulgare (grain sorghum) TRZAW = Triticum aestivum (winter wheat) VIOTR = Viola tricolor (wild pansy) ZEAMX = Zea mays (maize)

TABLE 50 Effect (% visual injury) of compound 1 (EC) and Rinskor ™ on weeds. Application Rate compound 1 (g ae/ha) 5 0 5 Rinskor ™ (g ae/ha) 0 5 5 ABUTH Obs 70 80 97 Exp 94 Δ 3 BRSNN Obs 50 20 85 Exp 60 Δ 25 CIRAR Obs 10 70 75 Exp 73 Δ 2 CYPES Obs 30 70 80 Exp 79 Δ 1 DIGSA Obs 0 0 20 Exp 0 Δ 20 HELAN Obs 80 85 100 Exp 97 Δ 3 KCHSC Obs 65 50 85 Exp 83 Δ 3 POLCO Obs 95 60 100 Exp 98 Δ 2 VIOTR Obs 10 10 20 Exp 19 Δ 1 ORYSA Obs 0 0 0 Exp 0 Δ 0 TRZAW Obs 10 0 0 Exp 10 Δ −10 ZEAMX Obs 5 0 10 Exp 5 Δ 5 g ae/ha = grams acid equivalent per hectare ABUTH = Abutilon theophrasti (velvetleaf) BRSNN = Brassica napus (spring rape) CIRAR = Cirsium arvense (Canadian thistle) CYPES = Cyperus esculentus (nutsedge) DIGSA = Digitaria sanguinalis (large crabgrass) HELAN = Helianthus annuus (sunflower) KCHSC = Kochia scoparia (kochia) ORYSA = Oryza sativa (common rice) POLCO = Polygonum convolvulus (wild buckwheat) TRZAW = Triticum aestivum (winter wheat) VIOTR = Viola tricolor (wild pansy) ZEAMX = Zea mays (maize)

TABLE 51 Effect (% visual injury) of compound 1 (EC) and quinclorac on weeds. Application Rate compound 1 (g ae/ha) 5 10 0 5 10 quinclorac (g ae/ha) 0 0 140 140 140 ABUTH Obs 50 60 0 60 70 Exp 50 60 Δ 10 10 AMARE Obs 75 97 10 100 100 Exp 78 97 Δ 23 3 BRSNW Obs 40 45 0 60 50 Exp 40 45 Δ 20 5 CHEAL Obs 90 100 5 97 100 Exp 91 100 Δ 7 0 EPHHL Obs 97 97 20 100 100 Exp 98 98 Δ 2 2 GLXMA Obs 95 100 30 100 100 Exp 97 100 Δ 4 0 IPOHE Obs 10 10 65 70 70 Exp 69 69 Δ 2 2 KCHSC Obs 60 60 0 70 70 Exp 60 60 Δ 10 10 SORVU Obs 0 50 0 20 10 Exp 0 50 Δ 20 −40 STEME Obs 70 70 10 100 100 Exp 73 73 Δ 27 27 VIOTR Obs 5 10 10 40 30 Exp 15 19 Δ 26 11 ORYSA Obs 0 10 0 0 10 Exp 0 10 Δ 0 0 TRZAW Obs 0 0 0 0 0 Exp 0 0 Δ 0 0 ZEAMX Obs 0 0 0 0 0 Exp 0 0 Δ 0 0 g ae/ha = grams acid equivalent per hectare; ABUTH = Abutilon theophrasti (velvetleaf); AMARE = Amaranthus retroflexus (pigweed); BRSNW = Brassica napus (winter rape); CHEAL = Chenopodium album L. (common lambsquarters); EPHHL = Euphorbia heterophylla (poinsettia); GLXMA = Glycine max (soybean); IPOHE = Ipomoea hederacea (ivyleaf morningglory); KCHSC = Kochia scoparia (kochia); ORYSA = Oryza sativa (common rice); SORVU = Sorghum vulgare (grain sorghum); STEME = Stellaria media (common chickweed); TRZAW = Triticum aestivum (winter wheat); VIOTR = Viola tricolor (wild pansy); ZEAMX = Zea mays (maize)

TABLE 52 Effect (% visual injury) of compound 1 (EC) and triclopyr-butotyl on weeds. Application Rate compound 1 (g ae/ha) 5 0 5 triclopyr-butotyl (g ae/ha) 0 280 280 ABUTH Obs 70 20 100 Exp 76 Δ 24 BRSNN Obs 50 80 100 Exp 90 Δ 10 CIRAR Obs 10 85 93 Exp 87 Δ 7 CYPES Obs 30 10 70 Exp 37 Δ 33 DIGSA Obs 0 0 30 Exp 0 Δ 30 ECHCG Obs 65 0 70 Exp 65 Δ 5 KCHSC Obs 65 50 90 Exp 83 Δ 8 STEME Obs 60 20 85 Exp 68 Δ 17 VIOTR Obs 10 65 95 Exp 69 Δ 27 ORYSA Obs 0 0 0 Exp 0 Δ 0 TRZAW Obs 10 15 10 Exp 24 Δ −14 ZEAMX Obs 5 10 30 Exp 15 Δ 16 g ae/ha = grams acid equivalent per hectare ABUTH = Abutilon theophrasti (velvetleaf) BRSNN = Brassica napus (spring rape) CIRAR = Cirsium arvense (Canadian thistle) CYPES = Cyperus esculentus (nutsedge) DIGSA = Digitaria sanguinalis (large crabgrass) ECHCG = Echinochloa crus-galli (barnyardgrass) KCHSC = Kochia scoparia (kochia) ORYSA = Oryza sativa (common rice) STEME = Stellaria media (common chickweed) TRZAW = Triticum aestivum (winter wheat) VIOTR = Viola tricolor (wild pansy) ZEAMX = Zea mays (maize)

TABLE 53 Effect (% visual injury) of compound 2 (EC) and 2,4-D EHE on weeds. Application compound 2 (g ae/ha) 5 10 0 5 10 Rate 2,4-D EHE (g ae/ha) 0 0 140 140 140 ALOMY Obs 0 0 0 10 15 Exp 0 0 Δ 10 15 AMARE Obs 88 100 75 100 95 Exp 97 100 Δ 3 −5 BRSNN Obs 30 55 65 87 83 Exp 76 84 Δ 11 −2 CYPES Obs 5 10 10 13 25 Exp 15 19 Δ −2 6 EPHHL Obs 35 75 5 55 100 Exp 38 76 Δ 17 24 IPOHE Obs 10 20 93 95 98 Exp 93 94 Δ 2 4 ORYSA Obs 10 18 10 15 23 Exp 19 26 Δ −4 −3 TRZAW Obs 3 3 0 5 8 Exp 3 3 Δ 3 5 ZEAMX Obs 3 3 0 0 5 Exp 3 3 Δ −3 3 g ae/ha = grams acid equivalent per hectare ALOMY = Alopecurus myosuroides (blackgrass) AMARE = Amaranthus retroflexus (pigweed) BRSNN = Brassica napus (spring rape) CYPES = Cyperus esculentus (nutsedge) EPHHL = Euphorbia heterophylla (poinsettia) IPOHE = Ipomoea hederacea (ivyleaf morningglory) ORYSA = Oryza sativa (common rice) TRZAW = Triticum aestivum (winter wheat) ZEAMX = Zea mays (maize)

TABLE 54 Effect (% visual injury) of compound 2 (EC) and 2,4-D EHE on weeds. Application Rate compound 2 (g ae/ha) 5 10 0 5 10 2,4-D EHE (g ae/ha) 0 0 400 400 400 AMARE Obs 65 60 80 95 97 Exp 93 83 Δ 2 14 BRSNW Obs 30 50 93 100 100 Exp 95 93 Δ 5 7 KCHSC Obs 30 75 50 70 70 Exp 65 73 Δ 5 −3 SASKR Obs 10 10 70 90 75 Exp 73 71 Δ 17 4 SINAR Obs 95 100 97 100 100 Exp 100 97 Δ 0 3 g ae/ha = grams acid equivalent per hectare AMARE = Amaranthus retroflexus (pigweed) BRSNW = Brassica napus (winter rape) KCHSC = Kochia scoparia (kochia) SASKR = Salsola iberica (Russian thistle) SINAR = Sinapis arvensis (wild mustard)

TABLE 55 Effect (% visual injury) of compound 2 (EC) and aminopyralid-TIPA on weeds. Application compound 2 5 10 0 5 10 Rate (g ae/ha) aminopyralid- 0 0 5 5 5 TIPA (g ae/ha) AVEFA Obs 0 0 0 10 13 Exp 0 0 Δ 10 13 DIGSA Obs 28 53 5 58 70 Exp 31 55 Δ 26 15 EPHHL Obs 35 75 18 90 75 Exp 46 79 Δ 44 −4 SORVU Obs 38 63 5 50 70 Exp 41 64 Δ 9 6 VIOTR Obs 15 40 48 65 60 Exp 55 69 Δ 10 −9 TRZAW Obs 3 3 0 3 0 Exp 3 3 Δ 0 −3 ZEAMX Obs 3 3 3 3 13 Exp 5 5 Δ −2 8 g ae/ha = grams acid equivalent per hectare AVEFA = Avena fatua (wild oat) DIGSA = Digitaria sanguinalis (large crabgrass) EPHHL = Euphorbia heterophylla (poinsettia) SORVU = Sorghum vulgare (grain sorghum) TRZAW = Triticum aestivum (winter wheat) VIOTR = Viola tricolor (wild pansy) ZEAMX = Zea mays (maize)

TABLE 56 Effect (% visual injury) of compound 2 (EC) and clopyralid on weeds. Application Rate compound 2 (g ae/ha) 5 10 0 5 10 clopyralid (g ae/ha) 0 0 100 100 100 AMARE Obs 88 100 28 100 100 Exp 91 100 Δ 9 0 BRSNN Obs 30 55 43 75 80 Exp 60 74 Δ 15 6 DIGSA Obs 28 53 0 40 45 Exp 28 53 Δ 13 -8 EPHHL Obs 35 75 5 65 65 Exp 38 76 Δ 27 −11 IPOHE Obs 10 20 35 60 68 Exp 42 48 Δ 19 20 ORYSA Obs 10 18 0 10 18 Exp 10 18 Δ 0 0 TRZAW Obs 3 3 0 5 3 Exp 3 3 Δ 3 0 ZEAMX Obs 3 3 0 0 0 Exp 3 3 Δ −3 −3 g ae/ha = grams acid equivalent per hectare AMARE = Amaranthus retroflexus (pigweed) BRSNN = Brassica napus (spring rape) DIGSA = Digitaria sanguinalis (large crabgrass) EPHHL = Euphorbia heterophylla (poinsettia) IPOHE = Ipomoea hederacea (ivyleaf morningglory) ORYSA = Oryza sativa (common rice) TRZAW = Triticum aestivum (winter wheat) ZEAMX = Zea mays (maize)

TABLE 57 Effect (% visual injury) of compound 2 (EC) and dicamba-DMA on weeds. Application compound 2 5 10 0 5 10 Rate (g ae/ha) dicamba-DMA 0 0 140 140 140 (g ae/ha) BRSNN Obs 30 55 50 65 88 Exp 65 78 Δ 0 10 CHEAL Obs 88 99 85 100 100 Exp 98 100 Δ 2 0 DIGSA Obs 28 53 0 40 65 Exp 28 53 Δ 13 13 EPHHL Obs 35 75 20 90 100 Exp 48 80 Δ 42 20 ORYSA Obs 10 18 5 13 20 Exp 15 22 Δ −2 −2 TRZAW Obs 3 3 0 0 0 Exp 3 3 Δ −3 −3 ZEAMX Obs 3 3 0 0 0 Exp 3 3 Δ −3 −3 g ae/ha = grams acid equivalent per hectare BRSNN = Brassica napus (spring rape) CHEAL = Chenopodium album L. (common lambsquarters) DIGSA = Digitaria sanguinalis (large crabgrass) EPHHL = Euphorbia heterophylla (poinsettia) ORYSA = Oryza sativa (common rice) TRZAW = Triticum aestivum (winter wheat) ZEAMX = Zea mays (maize)

TABLE 58 Effect (% visual injury) of compound 2 (EC) and fluroxypyr-MHE on weeds. Application compound 2 5 10 0 5 10 Rate (g ae/ha) fluroxypyr- 0 0 70 70 70 MHE (g ae/ha) ABUTH Obs 78 95 40 95 100 Exp 87 97 Δ 9 3 ALOMY Obs 0 0 0 3 8 Exp 0 0 Δ 3 8 AMARE Obs 88 100 70 100 100 Exp 96 100 Δ 4 0 AVEFA Obs 0 0 0 8 3 Exp 0 0 Δ 8 3 BRSNN Obs 30 55 15 63 75 Exp 41 62 Δ 22 13 CYPES Obs 5 10 0 5 18 Exp 5 10 Δ 0 8 DIGSA Obs 28 53 33 73 70 Exp 51 68 Δ 21 2 EPHHL Obs 35 75 18 50 85 Exp 46 79 Δ 4 6 IPOHE Obs 10 20 80 93 93 Exp 82 84 Δ 11 9 VIOTR Obs 15 40 80 87 88 Exp 83 88 Δ 4 −1 TRZAW Obs 3 3 0 5 0 Exp 3 3 Δ 3 −3 ZEAMX Obs 3 3 0 3 8 Exp 3 3 Δ 0 5 g ae/ha = grams acid equivalent per hectare ABUTH = Abutilon theophrasti (velvetleaf) ALOMY = Alopecurus myosuroides (blackgrass) AMARE = Amaranthus retroflexus (pigweed) AVEFA = Avena fatua (wild oat) BRSNN = Brassica napus (spring rape) CYPES = Cyperus esculentus (nutsedge) DIGSA = Digitaria sanguinalis (large crabgrass) EPHHL = Euphorbia heterophylla (poinsettia) IPOHE = Ipomoea hederacea (ivyleaf morningglory) TRZAW = Triticum aestivum (winter wheat) VIOTR = Viola tricolor (wild pansy) ZEAMX = Zea mays (maize)

TABLE 59 Effect (% visual injury) of compound 2 (EC) and MCPA EHE on weeds. Application compound 2 5 10 0 5 10 Rate (g ae/ha) MCPA EHE 0 0 140 140 140 (g ae/ha) ABUTH Obs 78 95 0 85 93 Exp 78 95 Δ 8 −3 AMARE Obs 88 100 70 100 100 Exp 96 100 Δ 4 0 BRSNN Obs 30 55 35 85 93 Exp 55 71 Δ 31 22 CYPES Obs 5 10 0 28 35 Exp 5 10 Δ 23 25 DIGSA Obs 28 53 10 40 60 Exp 35 57 Δ 5 3 EPHHL Obs 35 75 0 85 100 Exp 35 75 Δ 50 25 IPOHE Obs 10 20 80 88 83 Exp 82 84 Δ 6 −2 VIOTR Obs 15 40 60 70 78 Exp 66 76 Δ 4 2 ORYSA Obs 10 18 3 13 18 Exp 12 20 Δ 0 −2 TRZAW Obs 3 3 3 3 0 Exp 5 5 Δ −2 −5 ZEAMX Obs 3 3 0 0 5 Exp 3 3 Δ −3 3 g ae/ha = grams acid equivalent per hectare ABUTH = Abutilon theophrasti (velvetleaf) AMARE = Amaranthus retroflexus (pigweed) BRSNN = Brassica napus (spring rape) CYPES = Cyperus esculentus (nutsedge) DIGSA = Digitaria sanguinalis (large crabgrass) EPHHL = Euphorbia heterophylla (poinsettia) IPOHE = Ipomoea hederacea (ivyleaf morningglory) ORYSA = Oryza sativa (common rice) TRZAW = Triticum aestivum (winter wheat) VIOTR = Viola tricolor (wild pansy) ZEAMX = Zea mays (maize)

Example 8—Greenhouse Trials

Following the protocol in Example 1, compound 1 (EC) and Compound 2 (SC) were combined with diflufenzopyr and applied to kochia (Kochia scoparia, KCHSC) and the phytotoxicity of the herbicidal composition was measured. The condition of the test plants as compared with that of the control plants was determined visually and scored on a scale of 0 to 100 percent where 0 corresponds to no injury and 100 corresponds to complete kill. Colby's equation was used to determine the herbicidal effects expected from the mixtures. The results are summarized in Tables 60-61.

TABLE 60 Effect (% visual injury) of compound 1 (EC) and diflufenzopyr on kochia. Application compound 1 8.75 17.5 0 0 8.75 17.5 Rate diflufenzopyr 0 0 3.5 7 3.5 7 (g ae/ha) KCHSC Obs. 78 80 0 0 82 87 Exp. — — — — 78 80 Δ 4 7 g ae/ha = grams acid equivalents per hectare KCHSC = Kochia scoparia (kochia)

TABLE 61 Effect (% visual injury) of compound 2 (SC) and diflufenzopyr on kochia. Application compound 2 8.75 17.5 0 0 8.75 17.5 Rate diflufenzopyr 0 0 3.5 7 3.5 7 (g ae/ha) KCHSC Obs. 84 86 0 0 93 92 Exp. — — — — 84 86 Δ 10 6 g ae/ha = grams acid equivalents per hectare KCHSC = Kochia scoparia (kochia)

Example 9—Greenhouse Trials

Following the protocol in Example 1, compound 1 (EC) was combined with 2,3,5-TIBA or naptalam and applied to common rice (ORYSA), maize (ZEAMX) and winter wheat (TRZAW), and the phytotoxicity of the herbicidal compositions was measured. In addition, the efficacy of the herbicidal compositions on velvetleaf (Abutilon theophrasti, ABUTH), Chinese kale (Brassica alboglabra, BRSAG), brown mustard (Brassica juncea, BRSJU), rutabaga (Brassica napus var. napobrassica, BRSNA), spring rape (Brassica napus, BRSNN), Roundup Ready rape (Brassica napus, BRSNN-RR) winter rape (Brassica napus, BRSNW), turnip (Brassica rapa, BRSRR), Canadian thistle (Cirsium arvense CIRAR), common sunflower (Helianthus annuus, HELAN), wild buckwheat (Polygonum convolvulus, POLCO), wild pansy (Viola tricolor, VIOTR) was evaluated. The condition of the test plants as compared with that of the control plants was determined visually and scored on a scale of 0 to 100 percent where 0 corresponds to no injury and 100 corresponds to complete kill. Colby's equation was used to determine the herbicidal effects expected from the mixtures. The results are summarized in Tables 62-63.

TABLE 62 Effect (% visual injury) of compound 1 (EC) and 2,3,5-TIBA on weeds. Application Rate compound 1 (g ae/ha) 5 0 5 2,3,5-TIBA (g ai/ha) 0 140 140 ABUTH Obs 60 0 70 Exp 60 Δ 10 BRSAG Obs 15 0 30 Exp 15 Δ 15 BRSJU Obs 60 10 85 Exp 64 Δ 21 BRSNN Obs 50 5 60 Exp 53 Δ 8 BRSNN-RR Obs 35 0 65 Exp 35 Δ 30 BRSNW Obs 30 0 85 Exp 30 Δ 55 BRSRR Obs 50 20 65 Exp 60 Δ 5 HELAN Obs 70 0 97 Exp 70 Δ 27 POLCO Obs 65 0 80 Exp 65 Δ 15 VIOTR Obs 5 0 30 Exp 5 Δ 25 ORYSA Obs 5 0 10 Exp 5 Δ 5 TRZAW Obs 5 0 10 Exp 5 Δ 5 ZEAMX Obs 0 0 0 Exp 0 Δ 0 g ae/ha = grams acid equivalent per hectare; g ai/ha = grams active ingredient per hectare; ABUTH = Abutilon theophrasti (velvetleaf); BRSAG = Brassica alboglabra (Chinese kale); BRSJU = Brassica juncea (brown mustard); BRSNN = Brassica napus (spring rape); BRSNN-RR = Brassica napus (spring rape, Roundup Ready); BRSNW = Brassica napus (winter rape); BRSRR = Brassica rapa (turnip); HELAN = Helianthus annuus (common sunflower); ORYSA = Oryza sativa (common rice); POLCO = Polygonum convolvulus (wild buckwheat); TRZAW = Triticum aestivum (winter wheat); VIOTR = Viola tricolor (wild pansy); ZEAMX = Zea mays (maize)

TABLE 63 Effect (% visual injury) of compound 1 (EC) and naptalam on weeds. Application Rate compound 1 (g ae/ha) 5 0 5 naptalam (g ai/ha) 0 140 140 ABUTH Obs 60 0 65 Exp 60 Δ 5 BRSAG Obs 15 0 50 Exp 15 Δ 35 BRSNA Obs 65 0 100 Exp 65 Δ 35 BRSNN-RR Obs 35 0 63 Exp 35 Δ 28 BRSNW Obs 50 0 60 Exp 50 Δ 10 BRSRR Obs 50 0 70 Exp 50 Δ 20 CIRAR Obs 10 0 70 Exp 10 Δ 60 HELAN Obs 70 0 85 Exp 70 Δ 15 POLCO Obs 65 0 80 Exp 65 Δ 15 VIOTR Obs 5 0 30 Exp 5 Δ 25 ORYSA Obs 5 0 10 Exp 5 Δ 5 TRZAW Obs 5 0 5 Exp 5 Δ 0 ZEAMX Obs 0 0 0 Exp 0 Δ 0 g ae/ha = grams acid equivalent per hectare; g ai/ha = grams active ingredient per hectare; ABUTH = Abutilon theophrasti (velvetleaf); BRSAG = Brassica alboglabra (Chinese kale); BRSNA = Brassica napus var. napobrassica (rutabaga); BRSNN-RR = Brassica napus (spring rape, Roundup Ready); BRSNW = Brassica napus (winter rape); BRSRR = Brassica rapa (turnip); CIRAR = Cirsium arvense (Canadian thistle); HELAN = Helianthus annuus (sunflower); POLCO = Polygonum convolvulus (wild buckwheat); VIOTR = Viola tricolor (wild pansy); ORYSA = Oryza sativa (common rice); TRZAW = Triticum aestivum (winter wheat); ZEAMX = Zea mays (maize)

The compositions and methods of the appended claims are not limited in scope by the specific compositions and methods described herein, which are intended as illustrations of a few aspects of the claims and any compositions and methods that are functionally equivalent are intended to fall within the scope of the claims. Various modifications of the compositions and methods in addition to those shown and described herein are intended to fall within the scope of the appended claims. Further, while only certain representative compositions and method steps disclosed herein are specifically described, other combinations of the compositions and method steps also are intended to fall within the scope of the appended claims, even if not specifically recited. Thus, a combination of steps, elements, components, or constituents may be explicitly mentioned herein or less, however, other combinations of steps, elements, components, and constituents are included, even though not explicitly stated. The term “comprising” and variations thereof as used herein is used synonymously with the term “including” and variations thereof and are open, non-limiting terms. Although the terms “comprising” and “including” have been used herein to describe various embodiments, the terms “consisting essentially of” and “consisting of” can be used in place of “comprising” and “including” to provide for more specific embodiments of the invention and are also disclosed. Other than in the examples, or where otherwise noted, all numbers expressing quantities of ingredients, reaction conditions, and so forth used in the specification and claims are to be understood at the very least, and not as an attempt to limit the application of the doctrine of equivalents to the scope of the claims, to be construed in light of the number of significant digits and ordinary rounding approaches. 

1. A herbicidal composition comprising a synergistic herbicidally effective amount of (a) a pyridine carboxylic acid herbicide or an agriculturally acceptable N-oxide, salt, or ester thereof, and (b) a synthetic auxin herbicide selected from the group consisting of 2,4-D, 2,4-DB, MCPA, dichlorprop, mecoprop, dicamba, clopyralid, fluroxypyr, aminocyclopyrachlor, aminopyralid, quinclorac, agriculturally acceptable salts and esters thereof, and combinations thereof, wherein the pyridine carboxylic acid herbicide comprises a compound defined by Formula (I)

wherein X is N or CY, wherein Y is hydrogen or halogen R¹ is OR^(1′), wherein R^(1′) is hydrogen or C₁-C₄ alkyl, R² is chlorine; R³ and R⁴ are hydrogen; A is A3 or A15

R⁵ is hydrogen, halogen, C₁-C₄ alkyl, cyclopropyl, C₁-C₃ alkoxy, amino, C₁-C₄ alkylamino, OH, or CN; R⁶ and R^(6′) are independently hydrogen, halogen, C₁-C₄ alkyl, cyclopropyl, C₂-C₄ alkenyl, C₁-C₃ alkoxy, amino, OH, or CN; R⁷ and R^(7′) are independently hydrogen, halogen, C₁-C₄ alkyl, cyclopropyl, C₁-C₃ alkoxy, C₁-C₃ alkylthio, amino, C₁-C₄ alkylamino, or phenyl; R⁸ is hydrogen, C₁-C₃ alkyl, C₁-C₃ alkylcarbonyl, or phenyl; or an agriculturally acceptable N-oxide or salt thereof.
 2. The composition of claim 1, wherein the pyridine carboxylic acid herbicide comprises a compound defined by Formula (II)

wherein R¹ is OR^(1′), wherein R^(1′) is hydrogen or C₁-C₄ alkyl; R² is chlorine; R³ and R⁴ are hydrogen; A is A3 or A15; R⁵ is hydrogen, halogen, C₁-C₄ alkyl, cyclopropyl, C₁-C₃ alkoxy, amino, C₁-C₄ alkylamino, OH, or CN; R⁶ and R^(6′) are independently hydrogen, halogen, C₁-C₄ alkyl, cyclopropyl, C₂-C₄ alkenyl, C₁-C₃ alkoxy, amino, OH, or CN; R⁷ and R^(7′) are independently hydrogen, halogen, C₁-C₄ alkyl, cyclopropyl, C₁-C₃ alkoxy, C₁-C₃ alkylthio, amino, C₁-C₄ alkylamino, or phenyl; and R⁸ is hydrogen, C₁-C₃ alkyl, C₁-C₃ alkylcarbonyl, or phenyl; or an agriculturally acceptable N-oxide or salt thereof.
 3. The composition of claim 2, wherein R¹ is OR^(1′), wherein R^(1′) is hydrogen, or C₁-C₄ alkyl; R² is chlorine; R³ and R⁴ are hydrogen; A is A3 or A15; R⁵ is hydrogen, halogen, C₁-C₄ alkyl, C₁-C₃ alkoxy, amino, or C₁-C₄ alkylamino; R⁶ or R^(6′) are independently hydrogen, halogen, C₁-C₄ alkyl, cyclopropyl, C₂-C₄ alkenyl, C₁-C₃ alkoxy, or CN; R⁷ and R^(7′) are independently hydrogen, halogen, C₁-C₄ alkyl, alkoxy, C₁-C₃ alkylthio, cyclopropyl, amino, or C₁-C₄ alkylamino; and R⁸ is hydrogen, C₁-C₃ alkyl, or C₁-C₃ alkylcarbonyl.
 4. The composition of claim 1, wherein the pyridine carboxylic acid herbicide comprises a compound defined by Formula (III):

wherein X is N or CY, wherein Y is hydrogen or halogen; R¹ is OR^(1′), wherein R^(1′) is hydrogen or C₁-C₄ alkyl; R² is chlorine; R³ and R⁴ are hydrogen; R⁶ and R^(6′) are independently hydrogen, halogen, C₁-C₄ alkyl, cyclopropyl, C₂-C₄ alkenyl, C₁-C₃ alkoxy, OH, or CN; R⁷ and R^(7′) are independently hydrogen, halogen, C₁-C₄ alkyl, cyclopropyl, C₁-C₃ alkoxy, C₁-C₃ alkylthio, amino, C₁-C₄ alkylamino, or phenyl; and R⁸ is hydrogen, C₁-C₃ alkyl, C₁-C₃ alkylcarbonyl, or phenyl; or an agriculturally acceptable N-oxide or salt thereof.
 5. The composition of claim 1, wherein the pyridine carboxylic acid herbicide comprises one of the following:


6. The composition of claim 1, wherein the pyridine carboxylic acid herbicide comprises


7. (canceled)
 8. (canceled)
 9. The composition of claim 1, wherein the weight ratio of (a) to (b) is from 1:8000 to 300:1.
 10. (canceled)
 11. (canceled)
 12. (canceled)
 13. (canceled)
 14. (canceled)
 15. (canceled)
 16. (canceled)
 17. The composition of claim 1, further comprising a herbicidal safener.
 18. The composition of claim 1, further comprising an agriculturally acceptable adjuvant or carrier.
 19. The composition of claim 1, further comprising an additional pesticide.
 20. The composition of claim 1, wherein the active ingredients in the composition consist of (a) and (b).
 21. The composition of claim 1, which wherein the composition is provided as a herbicidal concentrate.
 22. A method of controlling undesirable vegetation comprising applying to vegetation or an area adjacent the vegetation or applying to soil or water to control the emergence or growth of vegetation a synergistic herbicidally effective amount of the composition of claim
 1. 23-50. (canceled)
 51. The method of claim 22, wherein the undesirable vegetation is controlled in spring barley (Hordeum vulgare, HORVS), winter wheat (Triticum aestivum, TRZAW), spring wheat (Triticum aestivum, TRZAS), common rice (Oryza sativa, ORYSA), maize (Zea mays, ZEAMX), or combinations thereof. 52-53. (canceled)
 54. The method of claim 22, wherein the undesirable vegetation includes a broadleaf weed. 55-59. (canceled) 